PH12015501633B1 - Pest-control composition and pest-control methods - Google Patents

Pest-control composition and pest-control methods Download PDF

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Publication number
PH12015501633B1
PH12015501633B1 PH12015501633A PH12015501633A PH12015501633B1 PH 12015501633 B1 PH12015501633 B1 PH 12015501633B1 PH 12015501633 A PH12015501633 A PH 12015501633A PH 12015501633 A PH12015501633 A PH 12015501633A PH 12015501633 B1 PH12015501633 B1 PH 12015501633B1
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Philippines
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group
formula
atom
oxide
compound represented
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PH12015501633A
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PH12015501633A1 (en
Inventor
Chie Shimizu
Masashi Kamezaki
Yoshihiko Nokura
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Sumitomo Chemical Co
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
    • A01N43/52—1,3-Diazoles; Hydrogenated 1,3-diazoles condensed with carbocyclic rings, e.g. benzimidazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles

Abstract

The present invention provides a composition for controlling pests having an excellent control efficacy on pests. A composition for controlling pests comprising a compound represented by the formula (1): wherein each of symbols are the same as defined in the Description, or N -oxide thereof; and a compound represented by the formula (2): wherein each of symbols are the same as defined in the Description; shows an excellent controlling efficacy on pests.

Description

with one or more halogen atoms;
R’* and R* are hydrogen atoms;
R’ is a C1-C3 alkyl group which may be substituted with one or more halogen atoms, a -C(OR'Y™); group, a halogen atom, or a hydrogen atom;
R> is a C1-C3 alkyl group which may be substituted with one or more halogen atoms, a -OR!® group, a -S(O)nR'° group, or a halogen atom;
R® is a cyano group, a -NR'®R'! group, a halogen atom, or a hydrogen atom;
R’ is a C1-C6 alkyl group which may be substituted with one or more halogen atoms;
R® is a -S(0).R' group, a cyano group, a halogen atom, or a hydrogen atom; and
R'® and R'' are the same or different to each other and each independently represent a Cl1-C3 alkyl group which may be substituted with one or more halogen atoms.
Item 4.
The composition for controlling pests according to
Item 1, wherein in the compound represented by the formula (1) or N-oxide thereof:
R' is an ethyl group;
R’ and R*! are hydrogen atoms;
R’ is a C1-C3 alkyl group which may be substituted with one or more halogen atoms, a -C(OR'®)s group, a halogen atom, or a hydrogen atom;
R® is a C1-C3 haloalkyl group, a -OR?*® group, a -
S(0)nR?*® group, or a halogen atom;
R® is a cyano group, a -NR'R' group, a halogen atom, or a hydrogen atom;
R’ is a C1-C6 alkyl group which may be substituted with one or more halogen atoms;
R® is a -S(0).R'® group, a cyano group, a halogen atom, ” 10 or a hydrogen atom;
RY and R'' are the same or different to each other and each independently represent a Cl1-C3 alkyl group which may be substituted with one or more halogen atoms; and
R*® is a C1-C3 haloalkyl group.
Item 5.
The composition for controlling pests according to : any one of Items 1 to 4, wherein in the compound represented by the formula (1) or N-oxide thereof,
A' is -NR'-.
Item 6.
The composition for controlling pests according to any one of Items 1 to 4, wherein in the compound represented by the formula (1) or N-oxide thereof,
A' is an oxygen atom.
Item 7.
The composition for controlling pests according to any one of Items 1 to 4, wherein in the compound represented by the formula (1) or N-oxide thereof,
A' is a sulfur atom.
Item 8.
The composition for controlling pests according to
Item 1, wherein the compound represented by the formula (1) or N-oxide thereof is a compound represented by the formula (1-2) or N-oxide thereof; the formula (1-2):
R1a / se (O)S rN SS.
R62” "p2a N N
R72 ( 1 2) wherein
R'™ represents a C1-C3 alkyl group;
A?* represents a nitrogen atom or =CR**-;
R??* represents a C1-C3 alkyl group which may be substituted with one or more halogen atoms, a -C(OR'??); group, a halogen atom, or a hydrogen atom;
R°® represents a C1-C3 haloalkyl group, a -OR**?* group,
a -S(0)R?% group, or a halogen atom;
R®® represents a cyano group, a -NR'"R'? group, a halogen atom, or a hydrogen atom;
R’® represents a C1-C6 alkyl group which may be substituted with one or more halogen atoms;
R** represents a -S(O)nR'®® group, a cyano group, a halogen atom, or a hydrogen atom;
R'®? and R'? are the same or different to each other and each independently represent a C1-C3 alkyl group which may be substituted with one or more halogen atoms;
R*°® represents a C1-C3 haloalkyl group; m independently represents 0, 1 or 2; and n represents 0, 1 or 2.
Item 9.
The composition for controlling pests according to
Item 1, wherein the compound represented by the formula (1) or N-oxide thereof is a compound represented by the formula (1-3) or N-oxide thereof; the formula (1-3):
HC,
CH,
RSP N nd __
A®TTS ON (1-3) wherein
A% represents a nitrogen atom or =CR® -;
R3® represents a Cl1-C3 alkyl group which may be substituted with one or more halogen atoms, a -C(OR'), group, a halogen atom, or a hydrogen atom;
R*® represents a Cl-C3 haloalkyl group, a -OR?*%® group, a -S(0)nR*® group, or a halogen atom;
R®® represents a -S(0).R'® group, a cyano group, a halogen atom, or a hydrogen atom;
ROP independently represents a Cl-C3 alkyl group which may be substituted with one or more halogen atoms;
R?® represents a C1-C3 haloalkyl group; m independently represents 0, 1 or 2; and n represents 0, 1 or 2.
Item 10.
The composition for controlling pests according to
Item 9, wherein in the compound represented by the formula (1-3) or N-oxide thereof,
R’® is a halogen atom or a hydrogen atom;
R*® is a C1-C3 perfluoroalkyl group, a -OR**®® group, or a -S(0).R*® group;
R**®® is a C1-C3 perfluoroalkyl group; and
R® is a halogen atom or a hydrogen atom.
Item 11.
The composition for controlling pests according to
Item 1, wherein the compound represented by the formula (1) or N-oxide thereof is a compound represented by the formula (1-4) or N-oxide thereof; the formula (1-4):
HaC,
CH,
SG
AZO N (1—4) wherein
A*° represents a nitrogen atom or =CR®*¢-;
RC represents a Cl1-C3 alkyl group which may be substituted with one or more halogen atoms, a -C(OR®¢), group, a halogen atom, or a hydrogen atom;
R*° represents a Cl-C3 haloalkyl group, a -OR*°° group, a -S(0).R?*°° group, or a halogen atom;
R®*® represents a -S(0).R!'°° group, a cyano group, a halogen atom, or a hydrogen atom;
R'°°¢ independently represents a C1-C3 alkyl group which may be substituted with one or more halogen atoms;
R*° represents a C1-C3 haloalkyl group; m independently represents 0, 1 or 2; and n represents 0, 1 or 2.
Item 12.
The composition for controlling pests according to
Item 11, wherein in the compound represented by the formula (1-4) or N-oxide thereof,
R’° is a halogen atom or a hydrogen atom;
R*® is a C1-C3 perfluoroalkyl group, a -OR’’® group, or a -S(0).R*’ group,
R*¢ is a C1-C3 perfluoroalkyl group, and
R® is a halogen atom or a hydrogen atom.
Item 13.
The composition for controlling pests according to any one of Items 1 to 7 wherein a weight ratio of the compound represented by the formula (1) to the compound represented by the formula (2) is in the range of 1,000:1 to 1:1,000.
Item 14.
The composition for controlling pests according to any one of Items 1 to 7 wherein a weight ratio of the compound represented by the formula (1) to the compound represented by the formula (2) is in the range of 500:1 to 1:10.
Item 15.
The composition for controlling pests according to
Item 8 wherein a weight ratio of the compound represented by the formula (1-2) to the compound represented by the formula (2) is in the range of 1,000:1 to 1:1,000.
Item 16.
The composition for controlling pests according to
Item 8 wherein a weight ratio of the compound represented by the formula (1-2) to the compound represented by the formula (2) is in the range of 500:1 to 1:10.
Item 17.
The composition for controlling pests according to
Item 9 or 10 wherein a weight ratio of the compound represented by the formula (1-3) to the compound represented by the formula (2) is in the range of 1,000:1 to 1:1,000.
Item 18.
The composition for controlling pests according to
Item 9 or 10 wherein a weight ratio of the compound represented by the formula (1-3) to the compound represented by the formula (2) is in the range of 500:1 to 1:10.
Item 19.
The composition for controlling pests according to
Item 11 or 12 wherein a weight ratio of the compound represented by the formula (1-4) to the compound represented by the formula (2) is in the range of 1,000:1 to 1:1,000.
Item 20.
The composition for controlling pests according to } Item 11 or 12 wherein a weight ratio of the compound : represented by the formula (1-4) to the compound represented by the formula (2) is in the range of 500:1 to 1:10.
Item 21.
A method for controlling pests, which comprises the step of applying an effective amount of the composition for controlling pests according to any one of Items 1 to to plants, plant seeds, bulbs, or a soil where plants grow.
The present invention can control pests. 20
MODE FOR CARRYING OUT THE INVENTION
A composition for controlling pests of the present invention comprises the compound represented by the formula (1) (hereinafter referred to as "the present fused heterocyclic compound") and the compound represented by the formula (2) (hereinafter referred to as "the present carboxamide compound").
For the present fused heterocyclic compound, "N- oxide" includes a compound wherein one or more ring- constituting nitrogen atoms in one or more the heterocyclic moieties are oxidized. The heterocyclic moieties which may form N-oxide includes, for example, the pyridine ring moiety.
For example, the nitrogen atom of the pyridine ring moiety of the formula (1) may be N-oxide (N—O).
Further, for example, in the formula (1), A? may be
N-oxide (N—O0).
The examples of each group as used herein are explained as follows.
In the following "Ca-Cb", "a" means the smallest number of the carbon atoms and "b" means the largest number of carbon atoms.
The term "Ca-Cb alkyl group" as used herein represents a straight- or branched-chain hydrocarbon group having "a" to "b" carbon atoms.
The term "Ca-Cb haloalkyl group represents a straight- or branched-chain hydrocarbon group having "a"
to "b" carbon atoms, wherein one or more hydrogen atoms attached to the carbon atoms are replaced with one or more halogen atoms. When two or more halogen atoms are attached to the carbon atoms, the halogen atoms may be the same or different.
The term "Ca-Cb alkoxy group" represents a straight- or branched-chain alkyl-O- group having "a" to "b" carbon atoms.
The term "Ca-Cb cycloalkyl group" represents a saturated cyclic hydrocarbon group having "a" to "b" carbon atoms.
In "which may be substituted with one or more atoms or groups selected from Group X" as used herein, when substituted with two or more atoms or groups selected from Group X, the atoms or groups selected from Group X may be the same or different to each other.
In "which may be substituted with one or more atoms or groups selected from Group Y" as used herein, when substituted with two or more atoms or groups selected from Group Y, the atoms or groups selected from Group Y may be the same or different to each other. : In "which may be substituted with one or more atoms or groups selected from Group W" as used herein, when substituted with two or more atoms or groups selected from Group W, the atoms or groups selected from Group W may be the same or different to each other.
In "which may be substituted with one or more halogen atoms” as used herein, when substituted with two or more halogen atoms, the halogen atoms may be the same or different to each other.
In "which may be substituted with one or more C1-C3 alkyl groups" as used herein, when substituted with two or more Cl-C3 alkyl groups, the Cl1-C3 alkyl groups may be the same or different to each other.
In the present fused heterocyclic compound, the term "halogen atom" includes a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
In the present fused heterocyclic compound, "a C1-Cé alkyl group which may be substituted with one or more (for example, 1 to 7, 1 to 5, or 1 to 3) atoms or groups selected from Group X" represents a straight- or branched-chain saturated hydrocarbon group having 1 to 6 carbon atoms, wherein one or more hydrogen atoms attached to the carbon atoms may optionally be replaced with one or more atoms or groups selected from Group X. When substituted with two or more atoms or groups selected from Group X, the atoms or groups selected from Group X may be the same or different to each other.
Examples of "a <C1-Cé alkyl group which may be substituted with one or more atoms or groups selected from Group X" include methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec- butyl group, tert-butyl group, pentyl group, neopentyl group, hexyl group, methoxymethyl group, ethoxymethyl group, propyloxymethyl group, isopropyloxymethyl group, butyloxymethyl group, sec-butyloxymethyl group, tert- butyloxymethyl group, 2-methoxyethyl group, 2-ethoxyethyl group, 2-propyloxyethyl group, 2-isopropyloxyethyl group, 2-butyloxyethyl group, 2-sec-butyloxyethyl group, 2-tert- butyloxyethyl group, trifluoromethyl group, trichloromethyl group, 2-fluoroethyl group, 2,2- difluoroethyl group, 2,2,2-trifluoroethyl group and pentafluoroethyl group, 2-hydroxyethyl group, cyclopropylmethyl group, l-methylcyclopropylmethyl group, 2,2-difluorocyclopropylmethyl group, trimethoxymethyl group, triethoxymethyl group etc. Examples of subgroups such as "a C1-C3 alkyl group which may be substituted with one or more atoms or groups selected from Group X" may be selected from the above, depending on the indicated number of carbon atom.
In the present fused heterocyclic compound, "a Cl-Cé alkyl group which may be substituted with one or more (for example, 1 to 7, 1 to 5, or 1 to 3) halogen atoms " represents a straight- or branched-chain hydrocarbon group having 1 to 6 carbon atoms, wherein one or more hydrogen atoms attached to the carbon atoms may optionally be replaced with one or more halogen atoms.
When substituted with two or more halogen atoms, the halogen atoms may be the same or different to each other.
Examples of "a CCl-Cé6 alkyl group which may be substituted with one or more halogen atoms" include methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, tert-butyl group, pentyl group, neopentyl group, hexyl group, trifluoromethyl group, trichloromethyl group, 2- fluorocethyl group, 2,2-difluoroethyl group, 2,2,2- trifluoroethyl group, and pentafluoroethyl group, heptafluoroisopropyl group etc. Examples of subgroups such as "a C1-C3 alkyl group which may be substituted with one or more halogen atoms" may be selected from the above, depending on the indicated number of carbon atom.
In the present fused heterocyclic compound, examples of "a Cl-Cé alkyl group which may be substituted with one or more (for example, 1 to 7, 1 to 5, or 1 to 3) atoms or groups selected from Group W" include methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, tert-butyl group, pentyl group, neopentyl group, hexyl group, trifluoromethyl group, trichloromethyl group, 2-fluoroethyl group, 2,2- difluoroethyl group, 2,2,2-trifluoroethyl group, pentafluoroethyl group, methoxymethyl group, ethoxymethyl group, propyloxymethyl group, isopropyloxymethyl group, butyloxymethyl group, sec-butyloxymethyl group, isobutyloxymethyl group, tert-butyloxymethyl group, methoxyethyl group, ethoxyethyl group, propyloxyethyl group, isopropyloxyethyl group, butyloxyethyl group, sec- butyloxyethyl group, isobutyloxyethyl group, tert- butyloxyethyl group etc. When substituted with two or more atoms or groups selected from Group W, the atoms or groups selected from Group W may be the same or different to each other.
In the present fused heterocyclic compound, examples of "a Cl1-C6 alkyl group which may be substituted with one or more atoms or groups selected from Group Y" include methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, tert-butyl group, pentyl group, neopentyl group, hexyl dJroup, trifluoromethyl group, trichloromethyl group, 2- fluoroethyl group, 2,2-difluorocethyl group, 2,2,2-
trifluoroethyl group and pentafluoroethyl group, cyclopropylmethyl group, 1l-methylcyclopropylmethyl group, 2,2-difluorocyclopropylmethyl group etc. Examples of subgroups are selected from the above, depending on the indicated number of carbon atom.
In the present fused heterocyclic compound, examples of "a Cl1-Cé6 alkoxy group which may be substituted with one or more (for example, 1 to 7, 1 to 5, or 1 to 3) halogen atoms" includes methoxy group, trifluoromethoxy group, ethoxy group, 2,2,2-trifluoroethoxy group, propyloxy group, isopropyloxy group, butyloxy group, isobutyloxy group, sec-butyloxy group, tert-butyloxy group, pentyloxy group, and hexyloxy group.
In the present fused heterocyclic compound, examples of "a (C3-C6 cycloalkyl group which may be substituted with one or more (for example, 1 to 7, 1 to 5, or 1 to 3) halogen atoms" include cyclopropyl group, 2,2- difluorocyclopropyl group, 2,2-dichlorocyclopropyl group, 2,2-dibromocyclopropyl group, cyclobutyl group, cyclopentyl group, and cyclohexyl group.
In the present fused heterocyclic compound, examples of "a (C3-C6 cycloalkyl group which may be substituted with one or more (for example, 1 to 7, 1 to 5, or 1 to 3) halogen atoms or one or more (for example, 1 to 7, 1 to 5, or 1 to 3) C1l-C3 alkyl groups" include cyclopropyl group, l-methylcyclopropyl group, 2-methylcyclopropyl group, 1- fluorocyclopropyl group, 2,2-difluorocyclopropyl group, 2,2-dichlorocyclopropyl group, 2,2-dibromocyclopropyl group, cyclobutyl group, cyclopentyl group, and cyclohexyl group.
In the present fused heterocyclic compound, the term "a Cl-C3 haloalkyl group" represents a straight- or branched-chain hydrocarbon group having 1 to 3 carbon atoms, wherein one or more hydrogen atoms attached to the carbon atoms are replaced with one or more (for example, 1 to 7, 1 to 5, or 1 to 3) halogen atoms. When substituted with two or more halogen atoms, the halogen atoms may be the same or different to each other.
Examples of "a C1-C3 haloalkyl group" include fluoromethyl group, chloromethyl group, bromomethyl group, iodomethyl group, difluoromethyl group, dichloromethyl group, trifluoromethyl group, chlorodifluoromethyl group, bromodifluoromethyl group, trichloromethyl group, 2- fluoroethyl group, 2-chloroethyl group, 2-bromoethyl group, 2,2-difluoroethyl group, 2,2,2-trifluorocethyl group, pentafluorocethyl group, heptafluoropropyl group,
heptafluoroisopropyl group etc.
In the present fused heterocyclic compound, examples of "C1-C3 alkyl group" include methyl group, ethyl group, propyl group, and isopropyl group.
In the present fused heterocyclic compound, examples of "Cl-C3 perfluoroalkyl group" include trifluoromethyl group, pentafluoroethyl group, heptafluoropropyl group, and heptafluoroisopropyl group.
Examples of the present fused heterocyclic compound include as follows.
The compound represented by the formula (1), wherein
R' is a C1-Cé6 alkyl group which may be substituted with one or more atoms or groups selected from Group Y;
R’ and R* are hydrogen atoms;
R’> is a C1-C3 alkyl group which may be substituted with one or more halogen atoms, a -C(OR*); group, a halogen atom, or a hydrogen atom;
R> is a C1-C3 alkyl group which may be substituted with one or more halogen atoms, a -OR!?® group, a -S(0) R' group, a -CO,R' group, a -SFs group, or a halogen atom;
R® is a -OR' group, a -NR'R' group, a -CO,R'® group,
a -C(O)NR'R'' group, -OC(O)R', a cyano group, a halogen atom, or a hydrogen atom;
R’ is a C1-C6 alkyl group which may be substituted with one or more halogen atoms, a -CH,CO,R'® group, a C3-C6 cycloalkyl group, or a hydrogen atom;
R® is a C1-C3 alkyl group which may be substituted with one or more halogen atoms, a -OR' group, a -S(0)R"° group, a cyano group, a halogen atom, or a hydrogen atom;
RY and R'' are the same or different to each other and each independently represent a C1-C3 alkyl group which may be substituted with one or more halogen atoms or a hydrogen atom, except for a -S(0).R'® group wherein m is 1 or 2 and R' is a hydrogen atom; and
Group Y comprising: a (C3-C6 cycloalkyl group which may be substituted with one or more halogen atoms and a halogen atom; or N-oxide thereof.
The compound represented by the formula (1), wherein
R' is a C1-C3 alkyl group which may be substituted with one or more halogen atoms;
R?’ and R* are hydrogen atoms;
R® is a C1-C3 alkyl group which may be substituted with one or more halogen atoms, a -C(OR'Y); group, a halogen atom, or a hydrogen atom;
R® is a C1-C3 alkyl group which may be substituted with one or more halogen atoms, a -OR' group, a -S(O).R* group, or a halogen atom;
R® is a cyano group, a -NR'R'' group, a halogen atom, or a hydrogen atom;
R’ is a C1-C6 alkyl group which may be substituted with one or more halogen atoms;
R® is a -S(0).R'® group, a cyano group, a halogen atom, or a hydrogen atom; and
R'® and R'' are the same or different to each other and each independently represent a Cl1-C3 alkyl group which may be substituted with one or more halogen atoms; or N-oxide thereof.
The compound represented by the formula (1), wherein
R' is an ethyl group;
R’ and R* are hydrogen atoms;
R’ is a C1-C3 alkyl group which may be substituted with one or more halogen atoms, a -C(OR'Y); group, a halogen atom, or a hydrogen atom;
R> is a (C1-C3 haloalkyl group, a -OR?*® group, a -
S (0) wR?*° group, or a halogen atom;
R® is a cyano group, a -NR!R'' group, a halogen atom, or a hydrogen atom;
R’ is a C1-C6 alkyl group which may be substituted with one or more halogen atoms;
R® is a -S(0).R' group, a cyano group, a halogen atom, or a hydrogen atom;
R'® and RY are the same or different to each other and each independently represent a C1-C3 alkyl group which may be substituted with one or more halogen atoms; and
R*® is a C1-C3 haloalkyl group; or N-oxide thereof.
The compound represented by the formula (1), wherein
A' is -NR’-; or N-oxide thereof.
The compound represented by the formula (1), wherein
A' is -NR’ -;
R' is a C1-C6 alkyl group which may be substituted with one or more atoms or groups selected from Group Y;
R’ and R! are hydrogen atoms;
R® is a C1-C3 alkyl group which may be substituted with one or more halogen atoms, a -C(OR'Y); group, a halogen atom, or a hydrogen atom;
R° is a C1-C3 alkyl group which may be substituted with one or more halogen atoms, a -OR!® group, a -S(O)R' group, a -CO,R'® group, a -SFs group, or a halogen atom;
R® is a -OR' group, a -NR!°R!! group, a -CO,R'® group, a -C(O)NRR'" group, -0C(0O)R!, a cyano group, a halogen atom, or a hydrogen atom;
R’ is a C1-C6 alkyl group which may be substituted with one or more halogen atoms, a -CH,CO,R™® group, a C3-Cé6 cycloalkyl group, or a hydrogen atom;
R® is a C1-C3 alkyl group which may be substituted with one or more halogen atoms, a -OR' group, a -S(0).R'° group, a cyano group, a halogen atom, or a hydrogen atom;
R'® and R' are the same or different to each other and each independently represent a Cl-C3 alkyl group which may be substituted with one or more halogen atoms or a hydrogen atom, except for a -S(0),R'° group wherein m is 1 or 2 and R' is a hydrogen atom; and
Group Y comprising: a (C3-C6 cycloalkyl group which may be substituted with one or more halogen atoms, and a halogen atom; or N-oxide thereof.
The compound represented by the formula (1), wherein
A' is -NR’-;
R' is a C1-C3 alkyl group which may be substituted with one or more halogen atoms;
R’ and R* are hydrogen atoms;
R’ is a C1-C3 alkyl group which may be substituted with one or more halogen atoms, a -C(OR'); group, a halogen atom, or a hydrogen atom;
R® is a C1-C3 alkyl group which may be substituted with one or more halogen atoms, a -OR'® group, a -S(O)nR* group, or a halogen atom;
R® is a cyano group, a -NR'R'' group, a halogen atom, or a hydrogen atom;
R’ is a C1-C6 alkyl group which may be substituted with one or more halogen atoms;
R® is a -S(0).R'® group, a cyano group, a halogen atom, or a hydrogen atom; and
R'® and R' are the same or different to each other and each independently represent a C1-C3 alkyl group which may be substituted with one or more halogen atoms; or N-oxide thereof.
The compound represented by the formula (1), wherein
A' is -NR-;
R' is an ethyl group;
R?’ and R® are hydrogen atoms;
R®> is a C1-C3 alkyl group which may be substituted with one or more halogen atoms, a -C(OR'®); group, a halogen atom, or a hydrogen atom;
R> is a C1-C3 haloalkyl group, a -OR?*’® group, a - . S(0)wR*° group, or a halogen atom;
R® is a cyano group, a -NR'R'! group, a halogen atom, or a hydrogen atom,
R’ is a C1-C6 alkyl group which may be substituted with one or more halogen atoms;
R® is a -S(0).R'® group, a cyano group, a halogen atom, or a hydrogen atom;
R*® and R'* are the same or different to each other and each independently represent a Cl1-C3 alkyl group which may be substituted with one or more halogen atoms; and
R?® is a C1-C3 haloalkyl group; or N-oxide thereof.
The compound represented by the formula (1), wherein
A! is an oxygen atom; or N-oxide thereof.
The compound represented by the formula (1), wherein
A' is an oxygen atom;
R' is a C1-C6 alkyl group which may be substituted with one or more atoms or groups selected from Group Y;
R’ and R* are hydrogen atoms;
R® is a C1-C3 alkyl group which may be substituted with one or more halogen atoms, a -C(OR'®); group, a halogen atom, or a hydrogen atom;
R®> is a C1-C3 alkyl group which may be substituted with one or more halogen atoms, a -OR!® group, a -S(0)qR® group, a -CO,R'® group, a -SFs group, or a halogen atom;
R® is a -OR' group, a -NR'R'’ group, a -CO;R'® group,
a -C(O)NRYR'" group, -0C(O)R'Y, a cyano group, a halogen atom, or a hydrogen atom;
R’ is a C1-C6 alkyl group which may be substituted with one or more halogen atoms, a -CH,CO.R'® group, a C3-Cé cycloalkyl group, or a hydrogen atom;
R® is a C1-C3 alkyl group which may be substituted with one or more halogen atoms, a -OR!° group, a -S(O)aR"° group, a cyano group, a halogen atom, or a hydrogen atom;
R'® and R'' are the same or different to each other and each independently represent a Cl1-C3 alkyl group which may be substituted with one or more halogen atoms or a hydrogen atom, except for a -S(0).R'° group wherein m is 1 or 2 and R' is a hydrogen atom; and
Group Y comprising: a (C3-C6 cycloalkyl group which may be substituted with one or more halogen atoms, and a halogen atom; or N-oxide thereof.
The compound represented by the formula (1), wherein
A' is an oxygen atom;
R' is a C1-C3 alkyl group which may be substituted with one or more halogen atoms;
R?’ and R* are hydrogen atoms;
R’ is a C1-C3 alkyl group which may be substituted with one or more halogen atoms, a -C(OR'Y?); group, a halogen atom, or a hydrogen atom;
R> is a C1-C3 alkyl group which may be substituted with one or more halogen atoms, a -OR' group, a -S(0).R'° group, or a halogen atom;
R® is a cyano group, a -NR'R' group, a halogen atom, or a hydrogen atom;
R’ is a Cl-Cé6 alkyl group which may be substituted with one or more halogen atoms;R® is a -S(0)uR' group, a cyano group, a halogen atom, or a hydrogen atom; and
R'® and RY are the same or different to each other and each independently represent a Cl1-C3 alkyl group which may be substituted with one or more halogen atoms; or N-oxide thereof.
The compound represented by the formula (1), wherein
A’ is a sulfur atom;
R' is an ethyl group;
R*> and R* are hydrogen atoms;
R® is a C1-C3 alkyl group which may be substituted with one or more halogen atoms, a -C(OR?), group, a halogen atom, or a hydrogen atom;
R° is a (C1-C3 haloalkyl group, a -OR?*°® group, a -
S (0) wR*° group, or a halogen atom;
R® is a cyano group, a -NR'R' group, a halogen atom,
or a hydrogen atom;
R’ is a C1-C6 alkyl group which may be substituted with one or more halogen atoms;
R® is a -S(0).R' group, a cyano group, a halogen atom, or a hydrogen atom;
R' and R'' are the same or different to each other and each independently represent a Cl1-C3 alkyl group which may be substituted with one or more halogen atoms; and
R*° is a C1-C3 haloalkyl group; or N-oxide thereof.
The compound represented by the formula (1), wherein
A' is a sulfur atom; or N-oxide thereof.
The compound represented by the formula (1), wherein
A' is a sulfur atom;
R' is a C1-C6 alkyl group which may be substituted with one or more atoms or groups selected from Group Y;
R’ and R* are hydrogen atoms,
R’ is a C1-C3 alkyl group which may be substituted with one or more halogen atoms, a -C(ORY®); group, a halogen atom, or a hydrogen atom;
R> is a C1-C3 alkyl group which may be substituted with one or more halogen atoms, a -OR' group, a -S(0)uR' group, a -CO,R'® group, a -SFs group, or a halogen atom;
R® is a -OR' group, a -NR'R'' group, a -CO,R'® group, a -C(O)NR'YR'" group, -OC(O)R', a cyano group, a halogen atom, or a hydrogen atom;
R’ is a C1-C6 alkyl group which may be substituted with one or more halogen atoms, a -CH,CO.R'® group, a C3-C6 cycloalkyl group, or a hydrogen atom;
R® is a C1-C3 alkyl group which may be substituted with one or more halogen atoms, a -ORY group, a -S(0).R* group, a cyano group, a halogen atom, or a hydrogen atom;
R'® and R'' are the same or different to each other and each independently represent a Cl-C3 alkyl group which may be substituted with one or more halogen atoms or a hydrogen atom, except for a -S(O)uR'° group wherein m is 1 or 2 and R'® is a hydrogen atom; and
Group Y comprising: a C3-C6 cycloalkyl group which may be substituted with one or more halogen atoms, and a halogen atom; or N-oxide thereof.
The compound represented by the formula (1), wherein
A' is a sulfur atom;
R' is a C1-C3 alkyl group which may be substituted with one or more halogen atoms;
R®’ and R* are hydrogen atoms;
R® is a C1-C3 alkyl group which may be substituted with one or more halogen atoms, a -C(OR'); group, a halogen atom, or a hydrogen atom;
R® is a C1-C3 alkyl group which may be substituted with one or more halogen atoms, a -ORY group, a -S(0).R* group, or a halogen atom;
R® is a cyano group, a -NR'R'! group, a halogen atom, or a hydrogen atom;
R’ is a C1-C6 alkyl group which may be substituted with one or more halogen atoms;
R® is a -S(0).R' group, a cyano group, a halogen atom, or a hydrogen atom; and
R!® and R' are the same or different to each other and each independently represent a Cl1-C3 alkyl group which may be substituted with one or more halogen atoms; or N-oxide thereof.
The compound represented by the formula (1), wherein
A' is a sulfur atom;
R' is an ethyl group;
R’ and R* are hydrogen atoms;
R’ is a C1-C3 alkyl group which may be substituted with one or more halogen atoms, a -C(OR%), group, a halogen atom, or a hydrogen atom;
R® is a C1-C3 haloalkyl group, a -OR*® group, a -
S(0)wR*® group, or a halogen atom;
R® is a cyano group, a -NR'R'' group, a halogen atom, or a hydrogen atom;
R’ is a C1-C6 alkyl group which may be substituted with one or more halogen atoms;
R® is a -S(0).R'® group, a cyano group, a halogen atom, or a hydrogen atom;
R!® and R' are the same or different to each other and each independently represent a C1-C3 alkyl group which may be substituted with one or more halogen atoms; and
R*® is a C1-C3 haloalkyl group; or N-oxide thereof.
The compound represented by the formula (1-2):
Ra ren
Rea a2 ~N N
R72 (1-2) wherein
R'® represents a C1-C3 alkyl group;
A** represents a nitrogen atom or =CR®*-;
R’® represents a C1-C3 alkyl group which may be substituted with one or more halogen atoms, a -C (OR?) , group, a halogen atom, or a hydrogen atom;
R°® represents a C1-C3 haloalkyl group, a -OR*** group, a -S(0),R*®® group, or a halogen atom;
R®® represents a cyano group, a -NR'R'*® group, a
PEST-CONTROL COMPOSITION AND PEST - CONTROL METHODS = o
TECHNICAL FIELD ”
Jo ie
The present invention relates to a composition for = controlling pests and a method for controlling pests. o : BACKGROUND ART = | -
Hitherto, many compounds have been known as active ingredients in a composition for controlling pests: (The
Pesticide Manual-15th edition, published by British Crop
Protection Council (BCPC), ISBN 978-1-901396-18-8). 15 .
SUMMARY OF INVENTION | oo (PROBLEMS TO BE SOLVED BY INVENTION) -
An object of the present invention is to provide a composition for controlling pests having an excellent control efficacy on pests.
halogen atom, or a hydrogen atom;
R’? represents a Cl1-Cé alkyl group which may be substituted with one or more halogen atoms;
R® represents a -S(0).R'"® group, a cyano group, a halogen atom, or a hydrogen atom;
R'*?® and R'™? are the same or different to each other and each independently represent a C1-C3 alkyl group which may be substituted with one or more halogen atoms;
R*%? represents a C1-C3 haloalkyl group; m independently represents 0, 1 or 2; and n represents 0, 1 or 2; or N-oxide thereof.
The compound represented by the formula (1-3):
HiC_
CH, re OS _ a2" "SN (1-3) wherein
A’® represents a nitrogen atom or =CR® -;
RP represents a C1-C3 alkyl group which may be substituted with one or more halogen atoms, a -C(OR'); group, a halogen atom, or a hydrogen atom;
R*® represents a C1-C3 haloalkyl group, a -OR?*%® group, a -S(0)aR**® group, or a halogen atom;
R®® represents a -S(0).R'® group, a cyano group, a halogen atom, or a hydrogen atom;
R'°®? independently represents a C1-C3 alkyl group which may be substituted with one or more halogen atoms;
R°® represents a C1-C3 haloalkyl group; m independently represents 0, 1 or 2; and n represents 0, 1 or 2; or N-oxide thereof.
The compound represented by the formula (1-3), wherein
R® is a halogen atom or a hydrogen atom;
R*® is a C1-C3 perfluoroalkyl group, a -OR’*® group, or a -S(0)R*® group;
R*® is a C1-C3 perfluoroalkyl group; and
R® is a halogen atom or a hydrogen atom; or N-oxide thereof. - The compound represented by the formula (1-4):
HaC
CH;
RS¢ N is __
A270 N (1—4) wherein
A*° represents a nitrogen atom or =CR®®-;
R’® represents a C1-C3 alkyl group which may be substituted with one or more halogen atoms, a -C(OR'?°), group, a halogen atom, or a hydrogen atom;
R>° represents a C1-C3 haloalkyl group, a -OR?%® group,
a -S(0).R*’® group, or a halogen atom;
R®*® represents a -S(0).R'" group, a cyano group, a halogen atom, or a hydrogen atom;
R®¢ independently represents a C1-C3 alkyl group which may be substituted with one or more halogen atoms;
R*°° represents a C1-C3 haloalkyl group; m independently represents 0, 1 or 2; and n represents 0, 1 or 2; or N-oxide thereof.
The compound represented by the formula (1-4), wherein
R’® is a halogen atom or a hydrogen atom;
R°® is a C1-C3 perfluoroalkyl group, a -OR**® group, or a -S(0).R** group;
R?*°¢ is a C1-C3 perfluoroalkyl group; and
R®® is a halogen atom or a hydrogen atom; or N-oxide thereof.
Formula (1):
R
RE On, R?
RE“ "AZ TA N
RY (1)
The compound represented by the formula (1), wherein
A' is -NR’-, and R’ is a C1-C6 alkyl group which may be substituted with one or more halogen atoms, or a hydrogen atom; or N-oxide thereof.
The compound represented by the formula (1), wherein
A' is -NR’-, and R’ is a methyl group, an ethyl group, or a propyl group; or N-oxide thereof.
The compound represented by the formula (1), wherein
A! is -NR’-, and R’ is a methyl group; or N-oxide thereof.
The compound represented by the formula (1), wherein
A' is -NR’-, and R’ is a hydrogen atom; or N-oxide thereof.
The compound represented by the formula (1), wherein
A? is a nitrogen atom; or N-oxide thereof.
The compound represented by the formula (1), wherein
A? is =N(—0)-: (N-oxide).
The compound represented by the formula (1), wherein
A’ is =CR®-; or N-oxide thereof.
The compound represented by the formula (1), wherein
A*> is =CR®-, and R® is a C1-C3 alkoxy group, a C1-C3 alkylsulfonyl group, a halogen atom, or a hydrogen atom; or N-oxide thereof.
The compound represented by the formula (1), wherein
A* is =CR®-, and R® is a C1-C3 alkoxy group; or N-oxide thereof.
The compound represented by the formula (1), wherein
A* is =CR®-, and R® is a C1-C3 alkylsulfonyl group; or N-
oxide thereof.
The compound represented by the formula (1), wherein
A* is =CR®-, and R® is a halogen atom; or N-oxide thereof.
The compound represented by the formula (1), wherein
A’? is =CH-; or N-oxide thereof.
The compound represented by the formula (1), wherein
A' is -NR’-, and A? is a nitrogen atom; or N-oxide thereof.
The compound represented by the formula (1), wherein
A' is -NR’-, and A’ is =N(—0)-: (N-oxide).
The compound represented by the formula (1), wherein
A! is -NR’-, and A? is =CR®-; or N-oxide thereof.
The compound represented by the formula (1), wherein
A! is -NR’-, and A? is =CH-; or N-oxide thereof.
The compound represented by the formula (1), wherein
A' is an oxygen atom, and A? is a nitrogen atom; or N- oxide thereof.
The compound represented by the formula (1), wherein
A' is an oxygen atom, and A? is =N(—0)-: (N-oxide).
The compound represented by the formula (1), wherein
A' is an oxygen atom, and A? is =CR®-; or N-oxide thereof.
The compound represented by the formula (1), wherein
A' is an oxygen atom, and A? is =CH-; or N-oxide thereof.
The compound represented by the formula (1), wherein
A' is a sulfur atom, and A’ is a nitrogen atom; or N-oxide thereof.
The compound represented by the formula (1), wherein
A' is a sulfur atom, and A? is =N(—0)-: (N-oxide).
The compound represented by the formula (1), wherein
A! is a sulfur atom, and A? is =CR®-; or N-oxide thereof.
The compound represented by the formula (1), wherein
A! is a sulfur atom, and A? is =CH-; or N-oxide thereof. :
The compound represented by the formula (1), wherein
R' is a C1-C6 alkyl group which may be substituted with one or more halogen atoms or a C3-C6 cycloalkyl group which may be substituted with one or more halogen atoms; or N-oxide thereof.
The compound represented by the formula (1), wherein
R' is a C1-C3 alkyl group which may be substituted with one or more halogen atoms; or N-oxide thereof.
The compound represented by the formula (1), wherein
R' is a methyl group, an ethyl group, or a propyl group, an isopropyl group, a trifluoromethyl group, a 2,2,2- trifluoroethyl group, a cyclopropyl group, or a cyclopropylmethyl group; or N-oxide thereof.
The compound represented by the formula (1), wherein
R' is an ethyl group or a cyclopropylmethyl group; or N-
oxide thereof.
The compound represented by the formula (1), wherein
R' is a methyl group; or N-oxide thereof;
The compound represented by the formula (1), wherein
R' is an ethyl group; or N-oxide thereof.
The compound represented by the formula (1), wherein
R' is a propyl group; or N-oxide thereof.
The compound represented by the formula (1), wherein
R' is an isopropyl group; or N-oxide thereof.
The compound represented by the formula (1), wherein
R® is a C1-C6 alkyl group which may be substituted with one or more atoms or groups selected from Group X, a halogen atom, or a hydrogen atom; or N-oxide thereof.
The compound represented by the formula (1), wherein
R’ is a C1-C3 alkyl group which may be substituted with one or more halogen atoms, a -C(OR'?); group, a halogen atom, or a hydrogen atom; or N-oxide thereof.
The compound represented by the formula (1), wherein
R’ is a C1-C3 alkyl group which may be substituted with one or more halogen atoms or a hydrogen atom; or N-oxide thereof.
The compound represented by the formula (1), wherein
R’ is a C1-C3 alkyl group which may be substituted with one or more halogen atoms; or N-oxide thereof.
The compound represented by the formula (1), wherein
R’ is a -C(OR'); group; or N-oxide thereof.
The compound represented by the formula (1), wherein
R?® is a halogen atom; or N-oxide thereof.
The compound represented by the formula (1), wherein
R® is a hydrogen atom; or N-oxide thereof.
The compound represented by the formula (1), wherein
R’ is a methyl group, a trifluoromethyl group, a pentafluoroethyl group, a hexafluoropropyl group, a hexafluoroisopropyl group, a trimethoxymethyl group, a triethoxymethyl group, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, or a hydrogen atom; or N- oxide thereof.
The compound represented by the formula (1), wherein
R® is a trifluoromethyl group; or N-oxide thereof.
The compound represented by the formula (1), wherein
R’ is a trimethoxymethyl group, or N-oxide thereof;
The compound represented by the formula (1), wherein
R’ and R! are both hydrogen atoms; or N-oxide thereof.
The compound represented by the formula (1), wherein
R> and R* are both hydrogen atoms, and R’® is a C1-C3 alkyl group which may be substituted with one or more halogen atoms, a -C(OR'); group, a halogen atom, or a hydrogen atom; or N-oxide thereof.
Woe uma fel (= 20 45
The compound represented by the formula (1), wherein
R? and R* are both hydrogen atoms, and R?® is a hydrogen atom; or N-oxide thereof.
The compound represented by the formula (1), wherein
R2 and R* are both hydrogen atoms, and R? is a trifluoromethyl group; or N-oxide thereof.
The compound represented by the formula (1), wherein
RZ and R* are both hydrogen atoms, and R3? is a/ ‘trimeéthoxymethyl group; or N-oxide thereof. :
The compound represented by the formula (1), wherein
R> is a C1-C3 alkyl group which may be substituted with one Or more halogen atoms, a -OR!? group, a -S(O)mR'® group, a -CO2R!® group, a -SFs group, or a halogen atom; or N- oxide thereof.
The compound represented by the formula (1), wherein
R® is a C1-C3 alkyl group which may be substituted with one or more halogen atoms, a -OR!? group, a -S(0)aR!? group, . or a halogen atom; or N-oxide thereof.
The compound represented by the formula (1), wherein
R5 is a C1-C3 haloalkyl group, a c1-C3 haloalkoxy group, a
C1-C3 haloalkylsulfanyl group, a Cl-C3 haloalkylsulfinyl group, a Cl1-C3 haloalkylsulfonyl group, or a halogen atom; or N-oxide thereof.
The compound represented by the formula (1), wherein
R® is a C1-C3 perfluoroalkyl group, a C1-C3 perfluoroalkoxy group, a Cl-C3 perfluoroalkylsulfanyl group, a Cl1-C3 perfluoroalkylsulfinyl group, a C1-C3 perfluoroalkylsulfonyl group, or a halogen atom; or N- oxide thereof.
The compound represented by the formula (1), wherein
R® is a C1-C3 perfluoroalkyl group; or N-oxide thereof.
The compound represented by the formula (1), wherein
R®> is a C1-C3 perfluorocalkoxy group; or N-oxide thereof.
The compound represented by the formula (1), wherein
R°> is a C1-C3 perfluoroalkylsulfanyl group, a C1-C3 perfluoroalkylsulfinyl group, or a Cl-C3 perfluoroalkylsulfonyl group; or N-oxide thereof.
The compound represented by the formula (1), wherein
R® is a halogen atom; or N-oxide thereof.
The compound represented by the formula (1), wherein
R> is a trifluoromethyl group, -CF,CF;, -CF,CF.CF;, -
CF(CF3;),, -OCF;, -OCF,CF;, -SCF;, -S(0O)CF;, -S(0O),CF3;, -
SCF,CF;, -S(O)CF,CF;, -S(0),CF,CF;, -SF;, a fluorine atom, a chlorine atom, a bromine atom, or a iodine atom; or N- oxide thereof.
The compound represented by the formula (1), wherein
R® is a trifluoromethyl group; or N-oxide thereof.
The compound represented by the formula (1), wherein
R° is -CF,CF;; or N-oxide thereof.
(MEANS TO SOLVE PROBLEMS)
The present inventors have intensively studied to find out a composition for controlling pests having an excellent control efficacy on pests. As a result, they have found that a composition comprising a compound : represented by the following the formula (1) and a : compound represented by the following the formula (2) has an excellent controlling effect on pests.
Specifically, the present invention includes:
Item 1.
A composition for controlling pests comprising a ) : compound represented by the formula (1) or N-oxide thereof and a compound represented by the formula (2); oo 15 the formula (1):
R!
RE Ons, R2
RE” AZ” TA N
R? (1) wherein
A' represents -NR’-, an oxygen atom, or a sulfur atom;
A? represents a nitrogen atom or =CR®-;
R' represents a Cl1-C6 alkyl group which may be substituted with one or more atoms or groups selected
The compound represented by the formula (1), wherein
R’> is -SCF;; or N-oxide thereof.
The compound represented by the formula (1), wherein
R®> is -S(O)CF;; or N-oxide thereof.
The compound represented by the formula (1), wherein
R® is -S(0),CF;; or N-oxide thereof.
The compound represented by the formula (1), wherein
R® is a -OR' group, a -NRR! group, a -CO,R!® group, a -
C(O)NR"™R' group, a cyano group, a halogen atom, or a hydrogen atom; or N-oxide thereof.
The compound represented by the formula (1), wherein
R® is a cyano group, a -NR'R!! group, a halogen atom, or a hydrogen atom; or N-oxide thereof.
The compound represented by the formula (1), wherein
R® is a hydrogen atom; or N-oxide thereof.
The compound represented by the formula (1), wherein
R’> is a C1-C3 haloalkyl group, a Cl1-C3 haloalkoxy group, a
Cl-C3 haloalkylsulfanyl group, a Cl1-C3 haloalkylsulfinyl group, a Cl1-C3 haloalkylsulfonyl group, or a halogen atom, and R® is a hydrogen atom; or N-oxide thereof.
The compound represented by the formula (1), wherein
R° is a (C1-C3 perfluoroalkyl group, a C1-C3 perfluoroalkoxy group, a Cl1-C3 perfluoroalkylsulfanyl group, a Cl1-C3 perfluoroalkylsulfinyl group, a C1-C3 perfluoroalkylsulfonyl group, or a halogen atom, and R® is a hydrogen atom; or N-oxide thereof.
The compound represented by the formula (1), wherein
R’> is a C1-C3 perfluoroalkyl group, and R® is a hydrogen atom; or N-oxide thereof.
The compound represented by the formula (1), wherein
R®> is a C1-C3 perfluoroalkoxy group, and R® is a hydrogen atom; or N-oxide thereof.
The compound represented by the formula (1), wherein
R° is a C1-C3 perfluorocalkylsulfanyl group, a Cl1l-C3 perfluoroalkylsulfinyl group, or a Cl1-C3 perfluoroalkylsulfonyl group, and R° is a hydrogen atom; or N-oxide thereof.
The compound represented by the formula (1), wherein
A' is -NR’ -;
R’ is a methyl group;
A? is a nitrogen atom;
R' is a C1-C3 alkyl group which may be substituted with one or more halogen atoms;
R’ and R* are both hydrogen atoms;
R’ is a C1-C3 alkyl group which may be substituted with one or more halogen atoms, a -C(OR'); group, a halogen atom, or a hydrogen atom;
R> is a (C1-C3 perfluoroalkyl group, a Cl-C3 perfluorocalkoxy group, a Cl-C3 perfluoroalkylsulfanyl group, a Cl1-C3 perfluoroalkylsulfinyl group, a Cl1-C3 perfluoroalkylsulfonyl group, or a halogen atom, and
R® is a hydrogen atom; or N-oxide thereof.
The compound represented by the formula (1), wherein
A' is -NR-;
R’ is a methyl group;
A’ is =N(—0)-;
R' is a C1-C3 alkyl group which may be substituted with one or more halogen atoms;
R?> and R* are both hydrogen atoms;
R® is a C1-C3 alkyl group which may be substituted with one or more halogen atoms, a -C(OR'Y); group, a halogen atom, or a hydrogen atom;
R> is a (C1-C3 perfluoroalkyl group, a Cl1-C3 perfluoroalkoxy group, a Cl-C3 perfluoroalkylsulfanyl group, a Cl1-C3 perfluoroalkylsulfinyl group, a Cl1l-C3 perfluoroalkylsulfonyl group, or a halogen atom; and
R® is a hydrogen atom; (N-oxide) .
The compound represented by the formula (1), wherein oo 25 A' is -NR? -;
R’ is a methyl group;
A* is =CR®-;
R® is a C1-C3 alkoxy group, a C1l-C3 alkylsulfanyl group, a halogen atom, or a hydrogen atom;
R' is a C1-C3 alkyl group which may be substituted with one or more halogen atoms;
R’ and R* are both hydrogen atoms;
R® is a C1-C3 alkyl group which may be substituted with one or more halogen atoms, a -C(OR'’); group, a halogen atom, or a hydrogen atom;
R> is a C(1-C3 perfluoroalkyl group, a C1-C3 perfluorocalkoxy group, a Cl1-C3 perfluoroalkylsulfanyl group, a Cl1-C3 perfluoroalkylsulfinyl group, a Cl1-C3 perfluoroalkylsulfonyl group, or a halogen atom, and
R® is a hydrogen atom; or N-oxide thereof.
The compound represented by the formula (1), wherein
A' is an oxygen atom;
A? is a nitrogen atom;
R' is a C1-C3 alkyl group which may be substituted with one or more halogen atoms;
R?’ and R* are both hydrogen atoms;
R’ is a C1-C3 alkyl group which may be substituted with one or more halogen atoms, a -C(OR'Y); group, a halogen atom, or a hydrogen atom;
R> is a (C1-C3 perfluorocalkyl group, a Cl1-C3 perfluoroalkoxy group, a C1-C3 perfluorcalkylsulfanyl group, a Cl-C3 perfluoroalkylsulfinyl group, a C1-C3 perfluoroalkylsulfonyl group, or a halogen atom, and
R® is a hydrogen atom; or N-oxide thereof.
The compound represented by the formula (1), wherein
A' is an oxygen atom;
A’ is =N(—0)-;
R' is a C1-C3 alkyl group which may be substituted with one or more halogen atoms;
R? and R* are both hydrogen atoms;
R’ is a C1-C3 alkyl group which may be substituted with one or more halogen atoms, a -C (OR), group, a halogen atom, or a hydrogen atom;
R° is a C1-C3 perfluorocalkyl group, a Cl-C3 perfluorocalkoxy group, a Cl-C3 perfluorocalkylsulfanyl group, a Cl1l-C3 perfluorocalkylsulfinyl group, a Cl1-C3 perfluorocalkylsulfonyl group, or a halogen atom, and
R® is a hydrogen atom (N-oxide) .
The compound represented by the formula (1), wherein
A' is an oxygen atom;
A’ is =CR®-;
R® is a c1-c3 alkoxy group, a C1-C3 alkylsulfanyl group, a halogen atom, or a hydrogen atom;
R' is a C1-C3 alkyl group which may be substituted with one or more halogen atoms;
R’ and R* are both hydrogen atoms;
R’ is a C1-C3 alkyl group which may be substituted with one or more halogen atoms, a -C(OR'); group, a halogen atom, or a hydrogen atom;
R° is a C(C1-C3 perfluorocalkyl group, a C1-C3 perfluoroalkoxy group, a C1-C3 perfluoroalkylsulfanyl group, a C1-C3 perfluoroalkylsulfinyl group, a C1-C3 perfluoroalkylsulfonyl group, or a halogen atom; and
R® is a hydrogen atom; or N-oxide thereof.
The compound represented by the formula (1-2), wherein A** is a nitrogen atom; or N-oxide thereof.
The compound represented by the formula (1-2), wherein A*? is =N(—0)-: (N-oxide).
The compound represented by the formula (1-2), wherein A%*®* is =CR®*-; or N-oxide thereof.
The compound represented by the formula (1-2), wherein A** is =CH-; or N-oxide thereof.
The compound represented by the formula (1-2),
wherein R'™ is a methyl group; or N-oxide thereof.
The compound represented by the formula (1-2), wherein R'* is an ethyl group; or N-oxide thereof.
The compound represented by the formula (1-2), wherein R'® is a propyl group; or N-oxide thereof.
The compound represented by the formula (1-2), wherein R'® is an isopropyl group; or N-oxide thereof.
The compound represented by the formula (1-2), wherein R?* is a hydrogen atom; or N-oxide thereof.
The compound represented by the formula (1-2), wherein R?* is a trifluoromethyl group; or N-oxide thereof. k The compound represented by the formula (1-2), wherein R*®* is a C1-C3 perfluoroalkyl group, a Cl1-C3 perfluorocalkoxy group, a Cl-C3 perfluoroalkylsulfanyl group, a C1-C3 perfluoroalkylsulfinyl group, a C1-C3 perfluorocalkylsulfonyl group, or a halogen atom, and R®? is a hydrogen atom; or N-oxide thereof.
The compound represented by the formula (1-2), wherein R*®* is a trifluoromethyl group, and R®® is a hydrogen atom; or N-oxide thereof.
The compound represented by the formula (1-2), wherein R®® is -CF,CF,, and R®*® is a hydrogen atom; or N- oxide thereof.
The compound represented by the formula (1-2), wherein R* is -SCF;, and R*® is a hydrogen atom; or N-
oxide thereof.
The compound represented by the formula (1-2), wherein R** is -S(0O)CF;, and R** is a hydrogen atom; or N- oxide thereof.
The compound represented by the formula (1-2), wherein R®®* is -S(0),CF;, and R®*® is a hydrogen atom; or
N-oxide thereof.
The compound represented by the formula (1-2), wherein
A** is a nitrogen atom;
R'? is an ethyl group;
R*® is a hydrogen atom;
R** is a Cl1-C3 perfluoroalkyl group, a C1-C3 perfluoroalkoxy group, a Cl-C3 perfluoroalkylsulfanyl group, a Cl1-C3 perfluoroalkylsulfinyl group, a Cl1-C3 perfluoroalkylsulfonyl group, or a halogen atom; and
R®® is a hydrogen atom; or N-oxide thereof.
The compound represented by the formula (1-2), wherein
A* is =N(—0)-;
R'? is an ethyl group;
R** is a hydrogen atom;
R* is a (C1-C3 perfluoroalkyl group, a C1-C3 perfluoroalkoxy group, a Cl-C3 perfluoroalkylsulfanyl group, a C1-C3 perfluoroalkylsulfinyl group, a C1-C3 perfluoroalkylsulfonyl group, or a halogen atom; and
R® is a hydrogen atom: (N-oxide).
The compound represented by the formula (1-2), wherein
A** is =CR**-;
R® is a C1-C3 alkoxy group, a Cl-C3 alkylsulfanyl group, a halogen atom, or a hydrogen atom;
R'? is an ethyl group;
R* is a hydrogen atom;
R°* is a (€1-C3 perfluoroalkyl group, a Cl1-C3 perfluorocalkoxy group, a Cl1-C3 perfluoroalkylsulfanyl group, a C1-C3 perfluoroalkylsulfinyl group, a C1-C3 perfluorcalkylsulfonyl group, or a halogen atom; and
R®® is a hydrogen atom; or N-oxide thereof.
The compound represented by the formula (1-2), wherein
A%® is a nitrogen atom;
R'® is an ethyl group;
R*?* is a trifluoromethyl group;
R®®* is a C(C1-C3 perfluoroalkyl group, a C1-C3 perfluorocalkoxy group, a Cl-C3 perfluorocalkylsulfanyl group, a Cl1-C3 perfluoroalkylsulfinyl group, a C1-C3 perfluoroalkylsulfonyl group, or a halogen atom; and
R®® is a hydrogen atom; or N-oxide thereof.
The compound represented by the formula (1-2), wherein
A*® ig =N(—0)-;
R'® is an ethyl group;
R*® is a trifluoromethyl group;
R®* is a (C1-C3 perfluoroalkyl group, a C1-C3 perfluorocalkoxy group, a Cl-C3 perfluorocalkylsulfanyl group, a Cl1-C3 perfluoroalkylsulfinyl group, a C1-C3 perfluoroalkylsulfonyl group, or a halogen atom, and
R®® is a hydrogen atom: (N-oxide).
The compound represented by the formula (1-2), wherein
A% ig =CR®-;
R® is a C1-C3 alkoxy group, a Cl1-C3 alkylsulfanyl group, a halogen atom, or a hydrogen atom;
R'? is an ethyl group;
R*® is a trifluoromethyl group;
R®* is a (€1-C3 perfluoroalkyl group, a Cl1-C3 from Group X;
R?, R® and R® are the same or different to each other and each independently represent a Cl1-Cé6 alkyl group which may be substituted with one or more atoms or groups selected from Group X, a -OR' group, a -C(OR'®); group, a -S(0) xR group, a -S(0),NR'R' group, a -NR'R'! group, a -
NR'°CO,R™ group, a -NR!?C(0)R! group, a -CO,R' group, a -
C(O)R'® group, a -C(O)NR'R'' group, a -SFs group, a cyano group, a nitro group, a halogen atom, or a hydrogen atom;
R’ and R® are the same or different to each other and each independently represent a C1-Cé alkyl group which may be substituted with one or more atoms or groups selected from Group X, a -OR' group, a -S(0)R'® group, a -S(0),NR'™R'! group, a -NRR! group, a -NR'YCO,R'' group, a -NR'°C(0)R™ group, a -CORY group, a -C(O)R*® group, a -
C(O)NR'R'' group, -OC(O)R®, a -SFs group, a -SH group, a ] cyano group, a nitro group, a halogen atom, or a hydrogen atom, except for a case in which R® and R® are both hydrogen atoms;
R’ represents a C1-C6 alkyl group which may be substituted with one or more atoms or groups selected from Group W, a -CO,R*® group, a -C(0O)R' group, a -
CH,CO,R'™ group, a C3-C6 cycloalkyl group, or a hydrogen atom;
R® represents a C1-Cé6 alkyl group which may be perfluoroalkoxy group, a Cl-C3 perfluoroalkylsulfanyl group, a Cl1-C3 perfluoroalkylsulfinyl group, a Cl-C3 perfluorocalkylsulfonyl group, or a halogen atom; and
R®® is a hydrogen atom; or N-oxide thereof.
The compound represented by the formula (1-3), wherein A* is a nitrogen atom; or N-oxide thereof.
The compound represented by the formula (1-3), wherein A** is =N(—0)-: (N-oxide).
The compound represented by the formula (1-3), wherein A?®* is =CR®®-; or N-oxide thereof.
The compound represented by the formula (1-3), wherein A? is =CH-; or N-oxide thereof.
The compound represented by the formula (1-3), wherein R®® is a hydrogen atom; or N-oxide thereof.
The compound represented by the formula (1-3), wherein R*® is a trifluoromethyl group; or N-oxide thereof.
The compound represented by the formula (1-3), wherein R®® is a C1-C3 perfluoroalkyl group, a C1-C3 perfluoroalkoxy group, a C1-C3 perfluoroalkylsulfanyl group, a Cl-C3 perfluoroalkylsulfinyl group, a Cl-C3 perfluoroalkylsulfonyl group, or a halogen atom; or N- oxide thereof.
The compound represented by the formula (1-3),
wherein R®® is a trifluoromethyl group; or N-oxide thereof.
The compound represented by the formula (1-3), wherein R® is -CF,CF;; or N-oxide thereof.
The compound represented by the formula (1-3), wherein R®® is -SCF,; or N-oxide thereof.
The compound represented by the formula (1-3), wherein R®*® is -S(0O)CF,;; or N-oxide thereof.
The compound represented by the formula (1-3), wherein R®® is -S(0),CF,; or N-oxide thereof.
The compound represented by the formula (1-3), wherein
A* is a nitrogen atom;
R® is a hydrogen atom;
R®® is a C1-C3 perfluorocalkyl group, a Cl1l-C3 perfluorocalkoxy group, a Cl-C3 perfluoroalkylsulfanyl group, a Cl-C3 perfluorocalkylsulfinyl group, a C1-C3 perfluoroalkylsulfonyl group, or a halogen atom; or N-oxide thereof.
The compound represented by the formula (1-3), wherein
A is =N(—0)-;
R*® is a hydrogen atom; and
R®® is a (C1-C3 perfluoroalkyl group, a Cl1-C3 perfluorcalkoxy group, a C1-C3 perfluoroalkylsulfanyl group, a Cl-C3 perfluoroalkylsulfinyl group, a Cl-C3 perfluoroalkylsulfonyl group, or a halogen atom: (N- oxide) .
The compound represented by the formula (1-3), wherein
A*® ig =CR® -;
R® is a C1-C3 alkoxy group, a Cl-C3 alkylsulfanyl group, a halogen atom, or a hydrogen atom;
R’® is a hydrogen atom;
R® is a C1-C3 perfluorocalkyl group, a Cl1l-C3 perfluorocalkoxy group, a Cl-C3 perfluoroalkylsulfanyl group, a Cl-C3 perfluorocalkylsulfinyl group, a Cl1l-C3 perfluoroalkylsulfonyl group, or a halogen atom; or N-oxide thereof.
The compound represented by the formula (1-3), wherein
A* is a nitrogen atom;
R’® is a trifluoromethyl group;
R*® is a Cl1-C3 perfluorocalkyl group, a Cl-C3 perfluorocalkoxy group, a Cl-C3 perfluoroalkylsulfanyl group, a Cl1-C3 perfluorocalkylsulfinyl group, a Cl-C3 perfluorocalkylsulfonyl group, or a halogen atom;
or N-oxide thereof.
The compound represented by the formula (1-3), wherein
A®® is =N(—0)-;
R*® is a trifluoromethyl group;
R® is a C1-03 perfluoroalkyl group, a C1-C3 perfluoroalkoxy group, a Cl-C3 perfluoroalkylsulfanyl group, a C1-C3 perfluoroalkylsulfinyl group, a C1l-C3 perfluorocalkylsulfonyl group, or a halogen atom (N-oxide).
The compound represented by the formula (1-3), wherein
A* ig =CR®"-; :
R® is a C1-C3 alkoxy group, a Cl-C3 alkylsulfanyl group, a halogen atom, or a hydrogen atom;
R*® is a trifluoromethyl group;
RP is a (Cl1-C3 ©perfluoroalkyl group, a C1-C3 perfluoroalkoxy group, a Cl-C3 perfluoroalkylsulfanyl group, a Cl1-C3 perfluoroalkylsulfinyl group, a C1-C3 perfluorocalkylsulfonyl group, or a halogen atom; or N-oxide thereof.
The compound represented by the formula (1-4), wherein 2% is a nitrogen atom; or N-oxide thereof.
The compound represented by the formula (1-4), wherein A%® is =N(—0)-: (N-oxide).
The compound represented by the formula (1-4), wherein A2%° is =CR®®-; or N-oxide thereof.
The compound represented by the formula (1-4), wherein A%* is =CH-; or N-oxide thereof.
The compound represented by the formula (1-4), wherein R?® is a hydrogen atom; or N-oxide thereof.
The compound represented by the formula (1-4), wherein R* is a trifluoromethyl group; or N-oxide thereof.
The compound represented by the formula (1-4), wherein R’°® is a C1-C3 perfluoroalkyl group, a C1-C3 perfluoroalkoxy group, a Cl-C3 perfluoroalkylsulfanyl group, a Cl1l-C3 perfluoroalkylsulfinyl group, a Cl1l-C3 perfluoroalkylsulfonyl group, or a halogen atom, and Rec is a hydrogen atom; or N-oxide thereof.
The compound represented by the formula (1-4), wherein R°° is a trifluoromethyl group; or N-oxide thereof.
The compound represented by the formula (1-4), wherein R°¢ is -CF,CF;; or N-oxide thereof.
The compound represented by the formula (1-4), wherein R®® is -SCF;; or N-oxide thereof.
The compound represented by the formula (1-4), wherein R°° is -S(O)CF;; or N-oxide thereof.
The compound represented by the formula (1-4),
wherein R®° is -S(0),CF;, or N-oxide thereof.
The compound represented by the formula (1-4), wherein
A*® is a nitrogen atom;
R’® is a hydrogen atom;
R® is a C1-C3 perfluoroalkyl group, a C1-C3 perfluorocalkoxy group, a Cl1-C3 perfluoroalkylsulfanyl group, a Cl1-C3 perfluoroalkylsulfinyl group, a Cl1-C3 perfluoroalkylsulfonyl group, or a halogen atom; or N-oxide thereof.
The compound represented by the formula (1-4), wherein
A*® is =N(—0)-;
R*“ is a hydrogen atom; and
R® is a C1-C3 perfluorocalkyl group, a C1-C3 perfluorocalkoxy group, a Cl-C3 perfluoroalkylsulfanyl group, a C1-C3 perfluoroalkylsulfinyl group, a C1-C3 perfluorocalkylsulfonyl group, or a halogen atom: (N- oxide) .
The compound represented by the formula (1-4), wherein
A*® is =CR®*-;
R® is a C1-C3 alkoxy group, C1-C3 alkylsulfanyl group,
a halogen atom, or a hydrogen atom;
R’® is a hydrogen atom;
R® is a (C1-C3 perfluoroalkyl group, a C1-C3 perfluorocalkoxy group, a Cl1-C3 perfluoroalkylsulfanyl group, a C1-C3 perfluoroalkylsulfinyl group, a Cl1-C3 perfluorocalkylsulfonyl group, or a halogen atom; or N-oxide thereof.
The compound represented by the formula (1-4), wherein
A*® is a nitrogen atom;
R*® is a trifluoromethyl group; and
R® is a (C1-C3 perfluoroalkyl group, a Cl1-C3 perfluoroalkoxy group, a Cl-C3 perfluorocalkylsulfanyl group, a Cl1-C3 perfluorocalkylsulfinyl group, a C1-C3 perfluoroalkylsulfonyl group, or a halogen atom; or N-oxide thereof.
The compound represented by the formula (1-4), wherein
A*® is =N(—0)-;
R’° is a trifluoromethyl group; and
R® is a C1-C3 perfluoroalkyl group, a Cl-C3 perfluoroalkoxy group, a Cl-C3 perfluoroalkylsulfanyl group, a Cl1-C3 perfluoroalkylsulfinyl group, a C1-C3 perfluoroalkylsulfonyl group, or a halogen atom: (N- oxide) .
The compound represented by the formula (1-4), wherein
A*® is =CR®*"-;
R® is a C1-C3 alkoxy group, a C1-C3 alkylsulfanyl group, a halogen atom, or a hydrogen atom;
R’® is a trifluoromethyl group; and
R** is a Cl1-C3 perfluoroalkyl group, a C1-C3 perfluoroalkoxy group, a Cl1-C3 perfluoroalkylsulfanyl group, a Cl1-C3 perfluoroalkylsulfinyl group, a Cl1-C3 perfluoroalkylsulfonyl group, or a halogen atom; or N-oxide thereof.
Next, a process for preparing the present fused heterocyclic compound is explained.
The present fused heterocyclic compound and intermediate compounds can be prepared, for example, according to the below-mentioned (Process 1) to (Process 24). (Process 1)
A present fused heterocyclic compound of formula (1)
wherein n is 1 or 2 can be prepared by oxidizing a present fused heterocyclic compound of formula (1) wherein n is 0. & R? ong R? os R?
RS NN _ RS SN _ RS NO De
R¥ ™a% A° N RS” AZ A° N RS” TA? N
R* R* R¢ (1-n0) (1-n1) (1-n2) [wherein, each symbol is the same as defined in formula (1) 1]
A present fused heterocyclic compound of formula (1- nl) (when n is 1 in the formula (1)) can be prepared by oxidizing a present fused heterocyclic compound (1-no0) (when n is 0 in the formula (1)) with an oxidizing agent.
The reaction is usually carried out in the presence of a solvent.
Examples of the solvent to be used in the reaction include aliphatic hydrogenated hydrocarbons such as dichloromethane and chloroform; alcohols such as methanol and ethanol; acetic acid; water; and mixed solvents thereof.
Examples of the oxidizing agent to be used include sodium periodate and m-chloroperoxybenzoic acid.
In the reaction, the oxidizing agent is used usually within a range of 1 to 3 molar ratio(s) as opposed to 1 mole of the present fused heterocyclic compound (1-n0).
Preferably, the oxidizing agent is used within a range of 1 to 1.2 molar ratio(s) as opposed to 1 mole of the present fused heterocyclic compound (1-no0).
The reaction temperature is usually within a range of -20 to 80°C. The reaction period of the reaction is usually within a range of 0.1 to 12 hours.
When the reaction is completed, the reaction mixtures are extracted with organic solvent(s), and the resulting organic layers are, 1f necessary, worked up (for example, washing with an aqueous solution of a reducing agent (such as sodium sulfite and sodium thiosulfate) and/or an aqueous solution of a base (such as sodium hydrogen carbonate), drying and concentration) to isolate the present fused heterocyclic compound (1-nl).
The isolated present fused heterocyclic compound (1-nl) may be further purified, for example, by chromatography and recrystallization.
A present fused heterocyclic compound of formula (1- n2) (when n is 2 in the formula (1)) can be prepared by oxidizing the present fused heterocyclic compound of formula (1-nl) (when n is 1 in the formula (1)).
The reaction is usually carried out in the presence of a solvent.
Examples of the solvent to be used in the reaction substituted with one or more halogen atoms, a -OR'® group, a -S(0)uR'® group, a -NR™R' group, a -CO,R*® group, a -
C(O)RY group, a cyano group, a nitro group, a halogen atom, or a hydrogen atom;
RY and R'' are the same or different to each other and each independently represent a Cl1-Cé6 alkyl group which may be substituted with one or more atoms or groups selected from Group X or a hydrogen atom, except for a -
S(0)nR'® group wherein m is 1 or 2 and RY is a hydrogen atom; m independently represents 0, 1 or 2; and n represents 0, 1 or 2;
Group X comprising: a Cl-Cé6 alkoxy group which may be substituted with one or more halogen atoms, a C3-C6 cycloalkyl group which may be substituted with one or more halogen atoms or one or more Cl-C3 alkyl groups, a cyano group, a hydroxy group, and a halogen atom;
Group W comprising: a Cl-Cé6 alkoxy group which may be substituted with one or more halogen atoms, a C3-C6 cycloalkyl group which may be substituted include aliphatic hydrogenated hydrocarbons such as dichloromethane and chloroform; alcohols such as methanol and ethanol; acids such as acetic acid; water; and mixed solvents thereof.
Examples of the oxidizing agent to be used include m-chloroperoxybenzoic acid and hydrogen peroxide.
In the reaction, the oxidizing agent is used usually within a range of 1 to 4 molar ratio(s) as opposed to 1 mole of the present fused heterocyclic compound (1-nl).
Preferably, the oxidizing agent is used within a range of 1 to 2 molar ratio(s) as opposed to 1 mole of the present fused heterocyclic compound (1-nl).
The reaction temperature is usually within a range of -20 to 120°C. The reaction period of the reaction is usually within a range of 0.1 to 12 hours.
When the reaction is completed, the reaction mixtures are extracted with organic solvent(s), and the resulting organic layers are, if necessary, worked up (for example, washing with an aqueous solution of a reducing agent (such as sodium sulfite and sodium thiosulfate), an aqueous solution of a base (such as sodium hydrogen carbonate), drying and concentration) to isolate the present fused heterocyclic compound (1-n2).
The isolated present fused heterocyclic compound (1-n2) may be further purified, for example, by chromatography and recrystallization.
Also, the present fused heterocyclic compound of formula (1-n2) (when n is 2 in the formula (1)) can be prepared by oxidizing the present fused heterocyclic compound (1-n0) (when n is 0 in the formula (1)) with an oxidizing agent in one step (one-pot).
The reaction is usually carried out in the presence of a solvent.
Examples of the solvent to be used in the reaction include aliphatic hydrogenated hydrocarbons such as dichloromethane and chloroform; alcohols such as methanol and ethanol; acids such as acetic acid; water; and mixed solvents thereof.
Examples of the oxidizing agent to be used include m-chloroperoxybenzoic acid and hydrogen peroxide.
The reaction may be also carried out, if necessary, in the presence of a catalyst.
Examples of the catalyst to be used include sodium tungstate.
In the reaction, the oxidizing agent is used usually within a range of 2 to 5 molar ratio(s), and the catalyst is used usually within a range of 0.01 to 0.5 molar ratio(s), as opposed to 1 mole of the present fused heterocyclic compound (1-no0). Preferably, the oxidizing agent is used usually within a range of 2 to 3 molar ratio(s), and the catalyst is used usually within a range of 0.01 to 0.5 molar ratio(s), as opposed to 1 mole of the present fused heterocyclic compound (1-no0).
The reaction temperature is usually within a range of 0 to 120°C. The reaction period of the reaction is usually within a range of 0.1 to 12 hours.
When the reaction is completed, the reaction mixtures are extracted with organic solvent (s),. and the resulting organic layers are, if necessary, worked up (for example, washing with an aqueous solution of a reducing agent (such as sodium sulfite and sodium thiosulfate) and/or an aqueous solution of a base (such as sodium hydrogen carbonate), drying and concentration) - 15 to isolate the present fused heterocyclic compound (1-n2).
The isolated present fused heterocyclic compound (1-n2) may be further purified, for example, by chromatography and recrystallization. (Process 2)
A present fused heterocyclic compound can be prepared by reacting an intermediate compound (M1) with an intermediate compound (M2) or an intermediate compound (M18) to afford an intermediate compound (M3), followed by performing an intramolecular condensation of the obtained intermediate compound (M3). In this reaction, a : production of the intermediate compound (M3) and an intramolecular condensation thereon may be occurred concurrently, resulting in no confirmation of the intermediate compound (M3).
R! KR. ons R2 one RY 0 a wo, : NN oe or se rR 5 HR 1 3 ‘ Hr © N—4 oh Le
RE NH; - - OSA _R
TI M2} IM 18) a 4) Mi a a Tr NTR . H . ce - . 35 41 a RE Le
BEC Ce | Co 4 i. 3 Re ons RY os RE R o — 0 = os RY
V4 re Of . Sg RAN So nd NW cof NA I [pr
R* Rt RES AT ON (M 23 CME) at oo oF : [wherein, each symbol is the same as defined in the formula (1)]
The intermediate compound (M3) may be prepared by reacting the intermediate compound (M1) with the intermediate compound (M2) in the presence of a condensation agent.
This reaction is usually carried out in the presence of a solvent. Examples of the solvent to be used in the reaction include ethers such as 1,4-dioxane, diethyl ether, tetrahydrofuran (hereinafter, sometimes referred to as THF) and methyl tert-butyl ether; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, chlorobenzene; aromatic hydrocarbons such as toluene, benzene and
Xylene; esters such as ethyl acetate and butyl acetate; nitriles such as acetonitrile; aprotic polar solvents such as N,N-dimethylformamide (hereinafter, sometimes referred to as DMF), N-methylpyrrolidone (hereinafter, sometimes referred to as NMP) , 1,3-dimethyl-2- imidazolidinone and dimethyl sulfoxide (hereinafter, sometimes referred to as DMSO); and nitrogen-containing . aromatic compounds such as pyridine and quinoline; and mixed solvents thereof.
The condensation agent to be used include l-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride (hereinafter, sometimes referred to as EDC hydrochloride), 1,3-dicyclohexylcarbodiimide. The reaction may be also carried out, if necessary, in the presence of a catalyst.
Examples of the catalyst to be used include 1- hydroxybenzotriazole (hereinafter, sometimes referred to as HOBt).
In the reaction, the intermediate compound (M2) is used usually within a range of 0.5 to 2 molar ratio(s), the condensation agent is used usually within a range of 1 to 5 molar ratio(s), and the catalyst is used usually within a range of 0.01 to 1 molar ratio(s), as opposed to 1 mole of the intermediate compound (M1).
The reaction temperature is usually within a range of 0 to 120°C. The reaction period of the reaction is usually within a range of 0.1 to 24 hours.
When the reaction is completed, the reaction mixtures are added into water and are then extracted with organic solvent (s), and the resulting organic layers are concentrated; the reaction mixtures are added into water and the resulting solids are collected by filtration; or the solids formed in the reaction mixtures are collected by filtration, to isolate the intermediate compound (M3).
The isolated intermediate compound (M3) may be further purified, for example, by recrystallization and chromatography.
Also, the intermediate compound (M3) may be prepared by reacting the intermediate compound (M1) with the intermediate compound (M18).
This reaction is usually carried out in the presence of a solvent.
Examples of the solvent to be used in the reaction include ethers such as THF, ethyleneglycol dimethyl ether, methyl tert-butyl ether and 1,4-dioxane; aliphatic hydrocarbons such as hexane, heptane and octane; aromatic hydrocarbons such as toluene and xylene; halogenated hydrocarbons such as chlorobenzene; esters such as ethyl acetate and butyl acetate; nitriles such as acetonitrile; aprotic polar solvents such as DMF, NMP and DMSO; and mixed solvents thereof.
The reaction may be also carried out, if necessary, in the presence of a base.
Examples of the base to be used include alkali metal carbonates such as sodium carbonate and potassium carbonate; tertiary amines such as triethylamine and N,N- diisopropylethylamine; and nitrogen-containing aromatic compounds such as pyridine and 4-dimethylaminopyridine.
In the reaction, the intermediate compound (M18) is used usually within a range of 1 to 3 molar ratio(s), and the base is used usually within a range of 1 to 10 molar ratio(g), as opposed to 1 mole of the intermediate compound (M1).
The reaction temperature is usually within a range of -20 to 100°C. The reaction period of the reaction is usually within a range of 0.1 to 24 hours.
When the reaction 1s completed, the reaction mixtures are added into water and are extracted with organic solvent (s), and the resulting organic layers are, if necessary, worked up (for example, drying and concentration) to isolate the intermediate compound (M3).
The intermediate compound (M3) may be further purified, for example, by chromatography and recrystallization.
The present fused heterocyclic compound (1) can be prepared by performing an intramolecular condensation of the intermediate compound (M3). :
The reaction is usually carried out in the presence of a solvent. Examples of the solvent to be used in the reaction include ethers such as 1,4-dioxane, diethyl ether, THF and methyl tert-butyl ether; halogenated hydrocarbons such as dichloromethane, chloroform, carbon oo IR tetrachloride, 1,2-dichloroethane and chlorobenzene; aromatic hydrocarbons such as toluene, benzene and
Xylene; esters such as ethyl acetate and butyl acetate; nitriles such as acetonitrile; aprotic polar solvent such as DMF, NMP, 1,3-dimethyl-2-imidazolidinone and DMSO; nitrogen-containing aromatic compounds such as pyridine and quinoline; and mixed solvents thereof.
In the reaction, if necessary, a condensation agent, an acid, a base or a chlorinating agent may be used.
Examples of the condensation agent to be used include acid anhydrides such as acetic . anhydride, trifluoroacetic anhydride; EDC hydrochloride; a mixture of triphenylphosphine, base and carbon tetrachloride or
Co carbon tetrabromide; and a mixture of triphenylphosphine and azodiesters such as diethyl azodicarboxylate.
Examples of the acid to be used include sulfonic acids such as para-toluenesulfonic acid; carboxylic acids such as acetic acid; and polyphosphoric acid.
Examples of the base to be used include pyridine, picoline, 2,6-1lutidine and 1,8-diazabicyclo[5.4.0]-7- undecene (hereinafter, sometimes referred to as DBU), nitrogen-containing heterocyclic compounds such as 1,5- diazabicyclo[4.3.0] -5-nonene; tertiary amines such as triethylamine and N,N-diisopropylethylamine; and inorganic bases such as tripotassium phosphate, potassium : carbonate and sodium hydride. co :
Examples of the chlorinating agent to be used : include phosphorus oxychloride.
In the reaction, when a condensation agent is used, the condensation agent is used usually within a range of 1 to 5 molar ratio(s), and when an acid is used, the acid is used usually within a range of 0.1 to 5 molar ratio(s), and when a base is used, the base is used usually within a range of 1 to 5 molar ratio(s), and when a chlorinating agent is used, the chlorinating agent is used usually within a range of 1 to 5 molar ratio(s), as opposed to 1 mole of the intermediate compound (M3).
The reaction temperature is usually within a range of 0 to 200°C. The reaction period of the reaction is usually within a range of 0.1 to 24 hours.
When the reaction is completed, the reaction mixtures are added into water and are then extracted with organic solvent(s), and the resulting organic layers are concentrated; the reaction mixtures are added into water and the resulting solids are collected by filtration; or the solids formed in the reaction mixture are collected by filtration, to afford the present fused heterocyclic compound (1). The isolated the present fused heterocyclic compound (1) may be further purified, for example, by recrystallization and chromatography.
The present fused heterocyclic compound (1) may be prepared in one step (one-pot) by reacting the intermediate compound (M1) with the intermediate compound (M2) in the presence of a condensation agent.
This reaction is usually carried out in the presence of a solvent.
Examples of the solvent to be used in the reaction include ethers such as 1,4-dioxane, diethyl ether, THF, methyl tert-butyl ether; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1,2- dichloroethane and chlorobenzene; aromatic hydrocarbons such as toluene, benzene, xylene; esters such as ethyl acetate and butyl acetate; nitriles such as acetonitrile; aprotic polar solvent such as DMF, NMP, 1,3-dimethyl-2- imidazolidinone and DMSO; nitrogen-containing aromatic compounds such as pyridine and quinoline; and mixed with one or more halogen atoms, a hydroxy group, a halogen atom, and a cyano group; 5 the formula (2):
R2 o
H
Cr hee (2)
Hal RU he wherein
R! represents a hydrogen atom or a methyl group; and
R®’ represents a methyl group, a difluoromethyl group, or a trifluoromethyl group.
Item 2.
The composition for controlling pests according to
Item 1, wherein in the compound represented by the formula (1) or N-oxide thereof,
R' is a C1-C6 alkyl group which may be substituted with one or more atoms or groups selected from Group Y;
R’ and R* are hydrogen atoms; ) R® is a C1-C3 alkyl group which may be substituted with one or more halogen atoms, a -C(OR'); group, a halogen atom, or a hydrogen atom;
R’> is a C1-C3 alkyl group which may be substituted with one or more halogen atoms, a -OR' group, a -S(O0).R'
solvents thereof.
Examples of the condensation agent to be used include carbodiimides such as EDC hydrochloride and 1,3- dicyclohexylcarbodiimide.
The reaction may be carried out, if necessary, in the presence of a catalyst.
Examples of the catalyst to be used include 1- hydroxybenzotriazole.
In the reaction, the intermediate compound (M2) is used usually within a range of 0.5 to 2 molar ratio(s), the condensation agent is used usually within a range of 1 to 5 molar ratio(s) and the catalyst is used usually within a range of 0.01 to 1 molar ratio(s), as opposed to 1 mole of the intermediate compound (M1).
The reaction temperature is usually within a range of 0 to 200°C. The reaction period of the reaction is usually within a range of 0.1 to 24 hours.
When the reaction is completed, the reaction mixtures are added into water and are then extracted with organic solvent(s), and the resulting organic layers are concentrated; the reaction mixtures are added into water and the resulting solids are collected by filtration; or the solids formed in the reaction mixture are collected by filtration, to isolate the present fused heterocyclic compound (1). The isolated present fused heterocyclic compound (1) may be further purified, for example, by recrystallization and chromatography.
Also, the present fused heterocyclic compound (1) can be prepared in one step (one-pot) by reacting the intermediate compound (M1) with the intermediate compound (M18) .
The reaction is usually carried out in the presence or absence of a solvent.
Examples of the solvent to be used in the reaction include ethers such as THF, ethyleneglycol dimethyl ether, methyl tert-butyl ether and 1,4-dioxane; aliphatic hydrocarbons such as hexane, heptane and octane; aromatic hydrocarbons such as toluene and xylene; halogenated hydrocarbons such as chlorobenzene; esters such as ethyl acetate and butyl acetate; nitriles such as acetonitrile; aprotic polar solvents such as DMF, NMP and DMSO; and mixed solvents thereof.
The reaction may be also carried out, if necessary, in the presence of a base.
Examples of the base to be used include alkali metal carbonates such as sodium carbonate and potassium carbonate; tertiary amines such as triethylamine and N,N- diisopropylethylamine; and nitrogen-containing aromatic compounds such as pyridine and 4-dimethylaminopyridine.
In the reaction, the intermediate compound (M18) is used usually within a range of 1 to 3 molar ratio(s), and the base is usually within a range of 1 to 10 molar ratio(s), as opposed to 1 mole of the intermediate compound (M1).
The reaction temperature is usually within a range of 20 to 200°C. The reaction period of the reaction is usually within a range of 0.1 to 24 hours.
When the reaction is completed, the reaction mixtures are added into water and are extracted with organic solvent(s), and the resulting organic layers are, if necessary, worked up (for example, drying and concentration) to isolate the present fused heterocyclic compound (1). The isolated present fused heterocyclic compound (1) may be further purified, for example, by chromatography and recrystallization. (Process 3)
A present fused heterocyclic compound of formula (P20) (when A' represents a sulfur atom and A? represents a nitrogen atom in the formula (1)) can be prepared by reacting an intermediate compound (M9) with an intermediate compound (M2) or an intermediate compound (M18) to afford an intermediate compound (M14), followed by reacting the obtained intermediate compound (M14) with a sulfuring agent. = (0), rR? 0 _ = y Re R! R?
HO N ) 3 Rr (O)S R Sa
RS NH: (M2) rR Ho = | 5 {OS R
A | TX NT TRY Tr S>—{ p RA
R* "N° TCI or 2
R! RN ar © RENTS ON oe
M9) (O)S. R? M14) (P20)
Q wa a R®
Rt {M 18) [wherein, each symbol is the same as defined in the formula (1)]
The intermediate compound (M14) can be prepared by reacting the intermediate compound (M9) with the intermediate compound (M2) in the presence of a condensation agent.
The reaction is carried out usually in the presence or absence of a solvent.
Examples of the solvent to be used in the reaction include ethers such as THF, ethyleneglycol dimethyl ether, methyl tert-butyl ether and 1,4-dioxane; aliphatic hydrocarbons such as hexane, heptane and octane; aromatic hydrocarbons such as toluene and xylene; halogenated hydrocarbons such as chlorobenzene; esters such as ethyl acetate and butyl acetate; nitriles such as acetonitrile; aprotic polar solvents such as DMF, NMP and DMSO; nitrogen-containing aromatic compounds such as pyridine and quinoline; and mixed solvents thereof.
Examples of the condensation agent to be used include carbodiimides such as EDC hydrochloride and 1,3- dicyclohexylcarbodiimide, and BOP reagent (for exmaple, benzotriazol-1-yloxy-trisdimetylamino phosphonium) .
In the reaction, the intermediate compound (M2) is used usually within a range of 1 to 3 molar ratios) and the condensation agent is used usually within a range of 1 to 5 molar ratio(s), as opposed to 1 mole of the intermediate compound (M9).
The reaction temperature is usually within a range of 0 to 200°C. The reaction period of the reaction is usually within a range of 0.1 to 24 hours.
When the reaction is completed, the reaction mixtures are added into water and are extracted with organic solvent (s), and the resulting organic layers are, if necessary, worked up (for example, drying and concentration) to isolate the intermediate compound (M14).
The isolated intermediate compound (M14) may be further purified, for example, by chromatography and recrystallization.
Also, the intermediate compound (M14) can be prepared by reacting the intermediate compound (M9) with the intermediate compound (M18).
The reaction is carried out usually in the presence or absence of a solvent. If necessary, the reaction may be also carried out in the presence of a base.
Examples of the solvent to be used in the reaction include ethers such as THF, ethyleneglycol dimethyl ether, methyl tert-butyl ether and 1,4-dioxane, aliphatic hydrocarbons such as hexane, heptane and octane; aromatic hydrocarbons such as toluene and xylene; halogenated hydrocarbons such as chlorobenzene, esters such as ethyl acetate and butyl acetate; nitriles such as acetonitrile; i aprotic polar solvents such as DMF, NMP and DMSO; nitrogen-containing aromatic compounds such as pyridine and quinoline; and mixed solvents thereof.
Examples of the base to be used include alkali metal carbonates such as sodium carbonate and potassium carbonate; tertiary amines such as triethylamine and N,N- diisopropylethylamine; and nitrogen-containing aromatic compounds such as pyridine and 4-dimethylaminopyridine.
In the reaction, the intermediate compound (M18) is used usually within a range of 1 to 3 molar ratio(s), and the base is used usually within a range of 1 to 5 molar ratio (s), as opposed to 1 mole of the intermediate compound (M9).
The reaction temperature is usually within a range of 0 to 200°C. The reaction period of the reaction is usually within a range of 0.1 to 24 hours.
When the reaction is completed, the reaction mixtures are added into water and are extracted with organic solvent(s), and the resulting organic layers are, if necessary, worked up (for example, drying and concentration) to isolate the intermediate compound (M14).
The isolated intermediate compound (M14) may be further purified, for example, by chromatography and recrystallization.
The present fused heterocyclic compound (P20) can be prepared by reacting the intermediate compound (14) with a sulfurizing agent.
The reaction is carried out in the presence or absence of a solvent.
Examples of the solvent to be used in the reaction include ethers such as 1,4-dioxane, diethyl ether, tetrahydrofuran, methyl tert-butyl ether and diglyme; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichlorocethane and chlorobenzene; aromatic hydrocarbons such as toluene, benzene and xylene; nitriles such as acetonitrile; nitrogen-containing aromatic compounds such as pyridine, picoline, 1lutidine and quinoline; and mixed solvents thereof.
Examples of the sulfurizing agent to be used include phosphorus pentasulfide and Lawesson's reagent (2,4-bis- (4 -methoxyphenyl) -1,3-dithia-2,4-diphosphetane-2,4- disulfide).
In the reaction, the sulfurizing agent is used usually within a range of 1 to 3 molar ratio(s) as opposed to 1 mole of the intermediate compound (M14).
The reaction temperature is usually within a range of 0 to 200°C. The reaction period of the reaction is usually within a range of 1 to 24 hours.
When the reaction is completed, the reaction mixtures are added into water and are then extracted with organic solvent(s), and the resulting organic layers are concentrated; the reaction mixtures are added into water and the resulting solids are collected by filtration; or the solids formed in the reaction mixture are collected by filtration, to isolate the present fused heterocyclic compound (P20). The isolated present heterocyclic compound (P20) may be further purified, for example, by recrystallization and chromatography. (Process 4)
A present fused heterocyclic compound can be prepared by reacting an intermediate compound (M1) with an intermediate compound (M4) in the presence of an oxidizing agent.
R1
OS R? . 0 == 3 \ R 1
Ho NA rR, 4 (Ons, R
RS NH R R2 N iA R 1 (M1) M [wherein, each symbol is the same as defined in the formula (1)]
This reaction is usually carried out in the presence of a solvent.
Examples of the solvent to be used in the reaction include alcohols such as methanol and ethanol; ethers such as 1,4-dioxane, diethyl ether, THF and methyl tert- butyl ether; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1,2- dichloroethane and chlorobenzene; aromatic hydrocarbons such as toluene, benzene and xylene; esters such as ethyl acetate and butyl acetate; nitriles such as acetonitrile; aprotic polar solvent such as DMF, NMP, 1,3-dimethyl-2- imidazolidinone and DMSO; nitrogen-containing aromatic compounds such as pyridine and quinoline; and mixed solvents thereof.
The reaction may be also carried out, for necessary, in the presence of an acid.
Examples of the acid to be used in the reaction include sulfonic acids such as paratoluenesulfonic acid; carboxylic acids such as acetic acid; and polyphosphoric acid.
The reaction may be also carried out, if necessary, in the presence of a sulfite.
Examples of the sulfite to be used in the reaction include sulfites such as sodium hydrogen sulfite and sodium bisulfite.
Examples of the oxidizing agent to be used include oxygen (for example, molecular oxygen) , copper chloride (II) and DDQ.
In the reaction, the intermediate compound (M4) is used usually within a range of 1 to 2 molar ratio(s), the acid is used usually within a range of 0.1 to 2 molar ratio(s), the sulfites is used usually within a range of 1 to 5 molar ratio(s), and the oxidizing agent is used usually within a range of 1 to 5 molar ratio(s), as opposed to one mole of the intermediate compound (M1).
The reaction temperature is usually within a range of 0 to 200°C. The reaction period of the reaction is usually within a range of 1 to 24 hours.
When the reaction is completed, the reaction mixtures are added into water and are then extracted with organic solvent(s), and the resulting organic layers are concentrated; the reaction mixtures are added into water group, a -CO,R'® group, a -SFs group, or a halogen atom;
R® is a -OR' group, a -NR!R'' group, a -CO.R'Y group, a -C(O)NR'R'"™ group, -0C(O)RY, a cyano group, a halogen atom, or a hydrogen atom;
R’ is a C1-C6 alkyl group which may be substituted with one or more halogen atoms, a -CH,CO,R'® group, a C3-C6 cycloalkyl group, or a hydrogen atom,
R® is a C1-C3 alkyl group which may be substituted with one or more halogen atoms, a -OR® group, a -S(0)qR* - 10 group, a cyano group, a halogen atom, or a hydrogen atom;
R'® and R'' are the same or different to each other and each independently represent a Cl1-C3 alkyl group which may be substituted with one or more halogen atoms or a hydrogen atom, except for a -S(0).R'® group wherein m is 1 or 2 and R' is a hydrogen atom; and
Group Y comprising: a C3-C6 cycloalkyl group which may be substituted with one or more halogen atoms and a halogen atom.
Item 3.
The composition for controlling pests according to
Item 1, wherein in the compound represented by the formula (1) or N-oxide thereof,
R' is a C1-C3 alkyl group which may be substituted and the resulting solids are collected by filtration; or the solids formed in the reaction mixture are collected by filtration, to isolate the present fused heterocyclic compound (1). The isolated present heterocyclic compound (1) may be further purified, for example, by recrystallization and chromatography. (Process 5)
A present fused heterocyclic compound (1) (when n is 0 in the formula (1)) can be prepared by reacting an intermediate compound (M6) with a compound (M7) in the presence of a base.
R'-SH R!
REN K_F M7) N s,_f&
R®™ A 4 RE“ Saz AlN .
R
(M 6) (Hhn=0 [wherein, V? represents a halogen atom, and the other symbols are the same as defined in the formula (1)]
This reaction is usually carried out in the presence of a solvent.
Examples of the solvent to be used in the reaction include ethers such as THF, ethyleneglycol dimethyl ether, methyl tert-butyl ether and 1,4-dioxane; aromatic hydrocarbons such as toluene and xylene; nitriles such as acetonitrile; aprotic polar solvents such as DMF, NMP and
DMSO; water; and mixed solvents thereof.
Examples of the base to be used include alkali metal carbonates such as sodium carbonate and potassium carbonate; and alkali metal hydrides such as sodium hydride.
In the reaction, the compound (M7) is used usually within a range of 1 to 10 molar ratio(s), and the base is used usually within a range of 1 to 10 molar ratio(s), as opposed to 1 mole of the intermediate compound (M6).
The reaction temperature is usually within a range of 0 to 150°C. The reaction period of the reaction is usually within a range of 0.5 to 24 hours.
When the reaction is completed, the reaction mixtures are extracted with organic solvent(s), and the resulting organic layers are worked up (for example, drying and concentration) to isolate the present fused heterocyclic compound (1) (when n is 0 in the formula (1)). The isolated present fused heterocyclic compound (1) (when n is 0 in the formula (1)) may be further purified, for example, by chromatography and recrystallization.
In the reaction, V? is preferably a fluorine atom and a chlorine atom. (Process 6)
An intermediate compound (M6) can be prepared by reacting an intermediate compound (M1) with an intermediate compound (M19) or an intermediate compound (M39) to afford an intermediate compound (M20), followed by performing an intramolecular condensation of the obtained intermediate compound (M20). In this reaction, a production of the intermediate compound (M20) and an intermolecular condensation thereon may be occurred .concurrently, resulting in no confirmation of the intermediate compound (M20). vi Rr? v2 Re?
Oo = GC — y JR NR Rr? : HO N or co N V2 rR} rR ZZ NH; RA ] re =
XN wet emt ROL]
RS AZ! | TY NTRS fh RE “a2 at ©
M1 : 4 v2 R? v2 R? . Vv: RZ
Q = QQ = RES =.
R R R
A 3 A
HO {| or gq NL RS 27 A! nL
R R
(M19) (M 39) M6) (wherein, V2 represents a halogen atom, and the other each symbol is the same as defined in the formula (1)]
The intermediate compound (M20) can be prepared by using the intermediate compound (M19) instead of the intermediate compound (M2) according to Process 2.
The intermediate compound (M20) can be prepared by using the intermediate compound (M39) instead of the intermediate compound (M18) according to Process 2.
The intermediate compound (M6) can be prepared by using the intermediate compound (M20) instead of the intermediate compound (M3) according to Process 2.
Also, the intermediate compound (M6) can be prepared by using the intermediate compound (M19) instead of the intermediate compound (M2) according to Process 2 in one step (one-pot). Co Tee Ine :
Also, the intermediate compound (M6) can be also prepared by using the intermediate compound (M39) instead of the intermediate compound (M2) according to Process 2 in one step (one-pot).
In the reaction, V2 represents preferably a fluorine i5 atom or a chlorine atom. (Process 7)
An intermediate compound (M3) (when n is 0 in the formula (M3)) can be prepared by reacting an intermediate compound (M20) with a compound (M7). Also, the obtained intermediate compound (M3) can be - performed on intramolecular condensation to afford a present fused heterocyclic compound (1) (when n is 0 in the formula
CE
91
RZ 1 2 v2 3 R-sH 1 3
ZZ R S Z R
Re” Sa2 a1 © RS" Sa2 a1 ©
U th
M = (M20) ny (M3) n=0
R1-SH ! rR!
RS Z N oo > FR
RE“SA27A' N
Rr4 (Wn=0 [wherein, Vv? represents a halogen atom, and the other each symbol is the same as defined in the formula (1)]
The intermediate compound (M3) (when n is 0 in the formula (M3)) can be prepared by using the intermediate compound (M20) instead of the intermediate compound of formula (M6) according to Process 5.
The present fused heterocyclic compound (1) (when n is 0 in the formula (1)) can be prepared by using the intermediate compound (M3) (when n is 0 in the formula (M3)) instead of the intermediate compound (M3) according to Process 2.
Also, the present fused heterocyclic compound (1) (when n is 0 in the formula (1)) can be also prepared by using the intermediate compound (M20) instead of the intermediate compound (M6) according to Process 5 in one step (one-pot).
In the reaction, V? represents preferably a fluorine atom or a chlorine atom. (Process 8)
A present fused heterocyclic compound (1) (when n is 0 in the formula (1)) can be prepared by reacting an intermediate compound (M8) or a disulfide compound thereof, that is, an intermediate compound (M8') with a compound (M17) in the presence of a base.
HS R?
RY = N ee R1-L
TL p=
RS Sp? Al N M17)
R4 rR! (M8) ; s Rr?
R N —_ 4 F
Z ] A N i R3 R'-L RE a2 Al N \
REN N — M17) R g R2 (H)n=0 . $s R?
NF NTN Rs solo N/R
RE“AZTAT NN
RA ms) [wherein, IL represents a leaving group such as a chlorine atom, a bromine atom, an iodine atom, a trifluoromethanesulfonyloxy group or a methanesulfonyloxy group, and the other each symbol is the same as defined in the formula (1)]
This reaction is usually carried out in the presence of a solvent.
Examples of the solvent to be used in the reaction include ethers such as THF, ethyleneglycol dimethyl ether, methyl tert-butyl = ether and 1,4-dioxane; aromatic hydrocarbons such as toluene and xylene; nitriles such as acetonitrile; aprotic polar solvents such as DMF, NMP and
DMSO; and mixed solvents thereof.
Examples of the base to be used include an alkali metal or alkaline-earth metal hydrides such as sodium hydride, potassium hydride and calcium hydride; inorganic bases such as sodium carbonate and potassium carbonate; and organic bases such as triethylamine.
When the intermediate compound (M8') being the disulfide compound is used, the reaction is usually carried out in the presence of a reducing agent.
Examples of the reducing agent to be used in the reaction include hydroxymethanesulfinic acid sodium salt (Trade name: Rongalite).
In the reaction, the intermediate compound (M17) is used usually within a range of 1 to 10 molar ratio(s), and the base is used usually within a range of 1 to 10 molar ratio(s), as opposed to 1 mole of the intermediate compound (M8). Also, when the intermediate compound (M8') being the disulfide compound is used, the intermediate compound (M17) is used usually within a range of 2 to 10 molar ratio(s), the base is used usually within a range of 2 to 10 molar ratio(s), and the reducing agent is used usually within a range of 1 to 5 molar ratio(s), as opposed to 1 mole of the intermediate compound (M8').
The reaction temperature is usually within a range of 0 to 100°C. The reaction period of the reaction is usually within a range of 0.1 to 24 hours.
When the reaction is completed, the reaction mixtures are extracted with organic solvent (s), and the resulting organic layers are worked up (for example, drying and concentration) to isolate the present fused heterocyclic compound (1) (when n is 0 in the formula (1)). The isolated present fused heterocyclic compound (1) (when n is 0 in the formula (1)) may be further purified, for example, by chromatography and recrystallization. (Process 9)
A present fused heterocyclic compound (1) (when n is 0 in the formula (1)) can be prepared by reacting an intermediate compound (M8') with a compound (M17'-1l) or a compound (M17'-2).
R*
RE. AZ Al N
TI; U N R3 RI
REINSTN == Ri-Mgv® s Rr?
Rr? (M1749) RS N= § Rr? “> JR
RAN = or RS SW2°A' ON
A R *
BN, 2 1 4 M17 -&)
RE“TAZT AT N (hn=0
Rt
Ma [wherein, V3 represents a chlorine atom, a bromine atom or an iodine atom; and the other each symbol is the same as defined in the formula (1)]
This reaction is usually carried out in the presence of a solvent.
Examples of the solvent to be used in the reaction include ethers such as THF, ethyleneglycol dimethyl ether, methyl tert-butyl ether and 1,4-dioxane; aromatic hydrocarbons such as toluene and xylene; nitriles such as acetonitrile; aprotic polar solvents such as DMF, NMP and
DMSO; and mixed solvents thereof.
In the reaction, the compound (M17'-1) is used usually within a range of 1 to 2 molar ratio(s) as opposed to 1 mole of the intermediate compound (M8').
Also, when the compound (M17'-2) is used, the compound (M17'-2) is used usually within a range of 1 to 2 molar ratio(s) as opposed to 1 mole of the intermediate compound (M8').
The reaction temperature is usually within a range of -80 to 100°C. The reaction period of the reaction is usually within a range of 0.1 to 24 hours.
When the reaction is completed, the reaction mixtures are extracted with organic solvent(s), and the resulting organic layers are worked up (for example, drying and concentration) to isolate the present fused heterocyclic compound (1) (when n is 0 in the formula (1)). The isolated present fused heterocyclic compound (1) (when n is 0 in the formula (1)) may be further purified, for example, by chromatography and recrystallization. (Process 10)
An intermediate compound (M8) can be prepared by reacting an intermediate compound (M6) with a sulfurizing agent. Also, an intermediate compound (M8') being a disulfide compound can be prepared by oxidizing an intermediate compound (M8).
R4
RE_AA_A! N ( 7 i 3 vz R? HS R? J _JR
RS N RS R
Z =\_ 3 AN =\_.3 § R?
A> RT > RR — { re
RE“SA2AT N RS“ A27AY NN RS
Rt Re ZZ N — 3 . > Rr (M6) (M8) RE“Sa2” A! ON
R4
M8) [wherein, V? represents a halogen atom, and the other each symbol is the same as defined in the formula (1)]

Claims (1)

: | 309 ) CLAIMS: /
1. A composition for controlling pests comprising a compound represented by the formula (1) or N-oxide thereof and one or more compounds selected from Group (A); the formula (1): R! ln TL — Se a R8“SAZ” "AT N R* (1) wherein A! represents -NR7-, an oxygen atom, or a sulfur atom; A? represents a nitrogen atom or =CRS8-; R! represents a Cl-C6 alkyl group which may be substituted with one or more atoms or groups selected from Group X; R2, R3 and R* are the same or different to each other and each independently represent a Cl-Cé alkyl group which may be substituted with one or more atoms or groups selected from Group X, a -OR!® group, a -C(OR!%) 3; group, a -S(O)mR!® group, a -S(0):NROR!! group, a -NRIOR1l group, a -NR°CO,R!l group, a -NR!°C(O)R!! group, a -CO2R!® group, a -C(O)RI® group, a -C(O)NRI°R!! group, a -SFs group, a cyano group, a nitro group, a halogen atom, or a hydrogen atom; R> and R® are the same or different to each other and
Claim 1, wherein the compound represented by the formula (1) or N-oxide thereof is a compound represented by the formula (1-2) or N-oxide thereof; the formula (1-2): Ra R53 x (OS __ Rea “N N Re (1—2) Ce wherein . R12 represents a Cl-C3 alkyl group; A?%2 represents a nitrogen atom or =CR32-; R32 represents a C1-C3 alkyl group which may be substituted with one or more halogen atoms, a -C(OR%2); group, a halogen atom, or a hydrogen atom; R32 represents a Cl1-C3 haloalkyl group, a -OR202 group, a -S(0)mR%2% group, or a halogen atom; R62 represents a cyano group, a -NRIaRUa group, a halogen atom, or a hydrogen atom; R72 represents a Cl-Cé6 alkyl group which may be substituted with one or more halogen atoms; R82 represents a -S(0)mR!%@ group, a cyano group, a halogen atom, or a hydrogen atom; R102 and R12 are the same or different to each other and each independently represent a C1-C3 alkyl group which may be substituted with one or more halogen atoms; R202 represents a C1-C3 haloalkyl group;
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